1-Benzyl­piperidin-4-one O-(2-bromo­benz­yl)oxime

Moreno-Fuquen, R.; Loaiza, A.E.; Diaz-Velandia, J.; Kennedy, A.R.; Morrison, C.A.

doi:10.1107/S1600536812040263

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3039

https://doi.org/10.1107/S1600536812040263

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1-Benzylpiperidin-4-one O-(2-bromobenzyl)oxime

Rodolfo Moreno-Fuquen,^a ^* Alix E. Loaiza,^b John Diaz-Velandia,^b Alan R. Kennedy ^c and Catriona A. Morrison ^c

^aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, ^bLaboratorio de Sintesis Orgánica, Facultad de Ciencias, Pontificia Universidad Javeriana, Bogota, DC, Colombia, and ^cWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
^*Correspondence e-mail: rodimo26@yahoo.es

(Received 10 September 2012; accepted 22 September 2012; online 29 September 2012)

In the title molecule, C₁₉H₂₁BrN₂O, the piperidone ring adopts a chair conformation with a total puckering amplitude Q_T of 0.554 (2) Å. The dihedral angle between the benzene rings is 64.10 (7)°. There are no significant intermolecular interactions.

Related literature

For the use of the oxime function in organic synthesis, see: Mikhaleva et al. (2006 ). For properties of the oxime function, see: Parthiban et al. (2011 ); Jayabharathi et al. (2011 ); Picard et al. (2000 ); For related structures, see: Parthiban et al. (2009 ); For details of ring-puckering conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₂₁BrN₂O
M_r = 373.29
Monoclinic, P 2₁ /c
a = 21.1586 (5) Å
b = 5.6731 (2) Å
c = 14.6425 (4) Å
β = 103.037 (3)°
V = 1712.31 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.41 mm⁻¹
T = 123 K
0.40 × 0.12 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.448, T_max = 1.000
9090 measured reflections
4525 independent reflections
3556 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.078
S = 1.03
4525 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812040263/gg2101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040263/gg2101Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812040263/gg2101Isup3.cml

checkCIF report

Comment top

The oxime function is a versatile intermediate in organic synthesis, for example, it can be readily transformed into important groups such as carbonyl, amino, nitro, cyano and can be used as a convenient protective group (Mikhaleva et al., 2006). The oxime function is also an important pharmacophore group, particularly oximes of the piperidone and their ethers possess a wide spectrum of biological activity such as cytotoxic (Parthiban et al., 2011), antimicrobial (Jayabharathi et al., 2011) and as an inhibitor of steroid-5-reductase (Picard et al., 2000). In our research group, we are interested in the synthesis of nitrogen containing compounds with potential biological activity such as oximes and isoxazoles. In order to accomplish this objective the 1-benzylpiperidin-4-one O-2-bromobenzyl oxime (I) was synthesized with the aim of evaluating its in vitro antimicrobial activity. The molecular structure of I is shown in Fig. 1. A single crystal XRD study has been carried out for (I) to confirm the sterochemistry stablished by NMR studies. Analisis of torsion angles, and least-square plane calculation, indicate that piperidone ring adopts a chair conformation with the smallest displacement parameters q₂= 0.078 (2) and q₃= 0.549 (2) Å, total puckering amplitude, Q_T= 0.554 (2) Å and φ₂= -176 (2)° (Cremer & Pople, 1975). This conformational behavior is similar to that reported by other similar systems (Parthiban et al., 2009). The least-squares fit of two phenyl rings C2/C3/C4/C5/C6/C7 and C14/C15/C16/C17/C18/C19 with a r.m.s deviation of fitted atoms of 0.0.009 and 0.004 Å respectively, shows a dihedral angle of 64.10 (7)° between the rings. The crystal packing shows no classical hydrogen bonds.

Related literature top

For the use of the oxime function in organic synthesis, see: Mikhaleva et al. (2006). For properties of the oxime function, see: Parthiban et al. (2011); Jayabharathi et al. (2011); Picard et al. (2000); For related structures, see: Parthiban et al. (2009); For details of ring-puckering conformational analysis, see: Cremer & Pople (1975).

Experimental top

In a two necks round bottom flask a mixture of 1-benzylpiperidin-4-one oxime (204 mg, 1 mmol), NaOH (80 mg, 2 mmol) in dry acetone (1.5 ml) was refluxed for 30 minutes, and then 2-bromobenzyl bromide (275 mg, 1,1 mmol) was added and subsequently stirred for 3 h. The reaction mixture was neutralized with acetic acid, extracted with AcOEt and dried with anhydrous Na₂SO₄. The combined organic layers were evaporated under low pressure to dryness. Purification of the crude mixture by flash column chromatography with 15% (v/v) AcOEt/hexane yielded compound 1 as a pale yellow solid (250 mg, 67% yield) mp 340.5 - 342.0 K. 1-benzylpiperidin-4-oneO-2-bromobenzyl oxime ¹H NMR (300 MHz) δ, 7.56 (dd, 1H, Ar—H), 7.43–7.27 (m, 7H, Ar—H), 7.17 (td, 1H, Ar—H), 5.16 (s, 2H, O—CH₂—Ar) 3.58 (s, 2H, N—CH₂—Ph), 2.73 (t, 2H, N=C—CH₂), 2.59 (t, 2H, N—CH₂), 2.56 (t, 2H, N—CH₂), 2.39 (t, 2H, N=C—CH₂). ¹³C-NMR δ, 158.3 (C=N), 138.0 (C), 137.5(C), 132.5 (Ar—H), 129.2, 129.1, 128.9, 128.3, 127.2, 122.7 (C—Br), 74.5 (O—CH₂—Ar), 62.5 (N—CH₂—Ar), 53.5 (N—CH₂), 52.4 (N—CH₂), 31.4 (N=C—CH₂), 25.5 (N=C—CH₂). MS—EI M⁺ m/z: 372.1, 374.1, 100%: 91.1.

Structure description top

For the use of the oxime function in organic synthesis, see: Mikhaleva et al. (2006). For properties of the oxime function, see: Parthiban et al. (2011); Jayabharathi et al. (2011); Picard et al. (2000); For related structures, see: Parthiban et al. (2009); For details of ring-puckering conformational analysis, see: Cremer & Pople (1975).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. An ORTEP-3 (Farrugia, 1997) plot of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

1-Benzylpiperidin-4-one O-(2-bromobenzyl)oxime top

Crystal data top

C₁₉H₂₁BrN₂O	F(000) = 768
M_r = 373.29	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 341(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 21.1586 (5) Å	Cell parameters from 4022 reflections
b = 5.6731 (2) Å	θ = 3.2–30.0°
c = 14.6425 (4) Å	µ = 2.41 mm⁻¹
β = 103.037 (3)°	T = 123 K
V = 1712.31 (9) Å³	Cut from large needle, colourless
Z = 4	0.40 × 0.12 × 0.05 mm

Data collection top

Oxford Diffraction Xcalibur E diffractometer	4525 independent reflections
Radiation source: fine-focus sealed tube	3556 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 30.0°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −29→28
T_min = 0.448, T_max = 1.000	k = −7→7
9090 measured reflections	l = −20→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0294P)² + 0.3261P] where P = (F_o² + 2F_c²)/3
4525 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

C₁₉H₂₁BrN₂O	V = 1712.31 (9) Å³
M_r = 373.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.1586 (5) Å	µ = 2.41 mm⁻¹
b = 5.6731 (2) Å	T = 123 K
c = 14.6425 (4) Å	0.40 × 0.12 × 0.05 mm
β = 103.037 (3)°

Data collection top

Oxford Diffraction Xcalibur E diffractometer	4525 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3556 reflections with I > 2σ(I)
T_min = 0.448, T_max = 1.000	R_int = 0.032
9090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.03	Δρ_max = 0.45 e Å⁻³
4525 reflections	Δρ_min = −0.69 e Å⁻³
208 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

	x	y	z	U_iso*/U_eq
Br1	0.089592 (10)	0.38045 (4)	0.610086 (15)	0.02227 (8)
O1	0.19320 (7)	0.9868 (3)	0.78376 (10)	0.0186 (3)
N1	0.25028 (8)	0.8872 (3)	0.84339 (13)	0.0182 (4)
N2	0.31211 (8)	1.2442 (3)	1.08828 (12)	0.0178 (4)
C1	0.15948 (10)	0.8022 (4)	0.72769 (15)	0.0185 (5)
H1A	0.1912	0.7023	0.7052	0.022*
H1B	0.1299	0.8716	0.6721	0.022*
C2	0.12070 (9)	0.6498 (4)	0.77892 (14)	0.0141 (4)
C3	0.08859 (9)	0.4501 (4)	0.73724 (14)	0.0155 (4)
C4	0.05440 (10)	0.3014 (4)	0.78332 (16)	0.0200 (5)
H4	0.0338	0.1645	0.7531	0.024*
C5	0.05072 (10)	0.3551 (4)	0.87379 (16)	0.0223 (5)
H5	0.0278	0.2538	0.9067	0.027*
C6	0.08033 (10)	0.5564 (4)	0.91680 (15)	0.0212 (5)
H6	0.0769	0.5950	0.9786	0.025*
C7	0.11498 (10)	0.7015 (4)	0.86974 (15)	0.0183 (5)
H7	0.1353	0.8389	0.9000	0.022*
C8	0.27666 (10)	1.0359 (4)	0.90613 (15)	0.0164 (4)
C9	0.25232 (10)	1.2752 (4)	0.92308 (15)	0.0202 (5)
H9A	0.2085	1.2990	0.8827	0.024*
H9B	0.2815	1.3968	0.9068	0.024*
C10	0.24949 (10)	1.3006 (4)	1.02568 (15)	0.0214 (5)
H10A	0.2372	1.4643	1.0375	0.026*
H10B	0.2158	1.1939	1.0393	0.026*
C11	0.32969 (10)	0.9998 (4)	1.07409 (15)	0.0188 (5)
H11A	0.2957	0.8934	1.0871	0.023*
H11B	0.3710	0.9610	1.1187	0.023*
C12	0.33726 (10)	0.9598 (4)	0.97427 (15)	0.0188 (5)
H12A	0.3747	1.0512	0.9634	0.023*
H12B	0.3455	0.7907	0.9649	0.023*
C13	0.30752 (11)	1.2827 (5)	1.18558 (15)	0.0246 (5)
H13A	0.2778	1.1639	1.2024	0.030*
H13B	0.2886	1.4403	1.1907	0.030*
C14	0.37229 (10)	1.2669 (4)	1.25436 (15)	0.0198 (5)
C15	0.38856 (11)	1.0734 (4)	1.31350 (15)	0.0222 (5)
H15	0.3588	0.9467	1.3102	0.027*
C16	0.44798 (12)	1.0645 (4)	1.37719 (16)	0.0258 (5)
H16	0.4587	0.9316	1.4171	0.031*
C17	0.49166 (11)	1.2485 (5)	1.38284 (16)	0.0263 (5)
H17	0.5321	1.2433	1.4272	0.032*
C18	0.47616 (11)	1.4401 (4)	1.32351 (17)	0.0249 (5)
H18	0.5062	1.5658	1.3263	0.030*
C19	0.41685 (11)	1.4481 (4)	1.26022 (16)	0.0229 (5)
H19	0.4065	1.5805	1.2199	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02297 (11)	0.02514 (14)	0.01779 (12)	−0.00154 (10)	0.00266 (8)	−0.00613 (10)
O1	0.0158 (7)	0.0169 (8)	0.0189 (8)	−0.0016 (6)	−0.0045 (6)	0.0019 (7)
N1	0.0136 (8)	0.0198 (10)	0.0194 (9)	0.0013 (7)	−0.0002 (7)	0.0026 (8)
N2	0.0140 (8)	0.0219 (10)	0.0160 (9)	0.0038 (7)	0.0006 (7)	−0.0017 (8)
C1	0.0175 (10)	0.0189 (11)	0.0169 (11)	−0.0036 (9)	−0.0011 (8)	−0.0009 (9)
C2	0.0122 (9)	0.0140 (11)	0.0142 (10)	0.0022 (8)	−0.0013 (7)	0.0010 (9)
C3	0.0129 (9)	0.0176 (11)	0.0143 (10)	0.0025 (8)	−0.0006 (8)	−0.0020 (9)
C4	0.0155 (10)	0.0183 (11)	0.0242 (12)	0.0008 (9)	0.0005 (9)	0.0012 (10)
C5	0.0188 (10)	0.0258 (13)	0.0219 (11)	−0.0007 (9)	0.0033 (9)	0.0071 (10)
C6	0.0207 (11)	0.0283 (13)	0.0139 (10)	0.0031 (9)	0.0025 (8)	0.0033 (10)
C7	0.0159 (10)	0.0199 (11)	0.0167 (11)	0.0003 (9)	−0.0015 (8)	−0.0018 (9)
C8	0.0147 (10)	0.0184 (11)	0.0159 (10)	−0.0007 (8)	0.0029 (8)	0.0007 (9)
C9	0.0203 (10)	0.0186 (12)	0.0183 (11)	0.0012 (9)	−0.0027 (9)	−0.0008 (10)
C10	0.0158 (10)	0.0253 (12)	0.0215 (11)	0.0039 (9)	0.0008 (9)	−0.0029 (10)
C11	0.0160 (10)	0.0214 (12)	0.0175 (11)	0.0010 (9)	0.0006 (8)	0.0001 (10)
C12	0.0139 (10)	0.0209 (12)	0.0199 (11)	0.0030 (9)	0.0004 (8)	−0.0018 (10)
C13	0.0197 (11)	0.0363 (14)	0.0179 (11)	0.0038 (10)	0.0046 (9)	−0.0026 (11)
C14	0.0184 (10)	0.0271 (13)	0.0144 (10)	0.0033 (9)	0.0050 (8)	−0.0037 (10)
C15	0.0264 (11)	0.0232 (13)	0.0176 (11)	−0.0035 (9)	0.0060 (9)	−0.0023 (10)
C16	0.0311 (13)	0.0288 (14)	0.0179 (11)	0.0036 (10)	0.0059 (10)	0.0048 (10)
C17	0.0211 (11)	0.0360 (15)	0.0199 (12)	0.0007 (10)	0.0010 (9)	−0.0027 (12)
C18	0.0242 (12)	0.0246 (13)	0.0258 (13)	−0.0055 (10)	0.0054 (10)	−0.0013 (11)
C19	0.0241 (11)	0.0227 (12)	0.0223 (12)	0.0039 (9)	0.0059 (9)	0.0038 (10)

Geometric parameters (Å, º) top

Br1—C3	1.908 (2)	C9—H9A	0.9900
O1—C1	1.420 (2)	C9—H9B	0.9900
O1—N1	1.437 (2)	C10—H10A	0.9900
N1—C8	1.279 (3)	C10—H10B	0.9900
N2—C11	1.462 (3)	C11—C12	1.523 (3)
N2—C13	1.466 (3)	C11—H11A	0.9900
N2—C10	1.466 (2)	C11—H11B	0.9900
C1—C2	1.504 (3)	C12—H12A	0.9900
C1—H1A	0.9900	C12—H12B	0.9900
C1—H1B	0.9900	C13—C14	1.509 (3)
C2—C3	1.389 (3)	C13—H13A	0.9900
C2—C7	1.393 (3)	C13—H13B	0.9900
C3—C4	1.382 (3)	C14—C19	1.384 (3)
C4—C5	1.379 (3)	C14—C15	1.392 (3)
C4—H4	0.9500	C15—C16	1.387 (3)
C5—C6	1.384 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.384 (3)
C6—C7	1.385 (3)	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.384 (3)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.492 (3)	C18—C19	1.382 (3)
C8—C12	1.500 (3)	C18—H18	0.9500
C9—C10	1.524 (3)	C19—H19	0.9500

C1—O1—N1	107.75 (15)	C9—C10—H10A	109.3
C8—N1—O1	110.33 (17)	N2—C10—H10B	109.3
C11—N2—C13	110.74 (18)	C9—C10—H10B	109.3
C11—N2—C10	109.94 (17)	H10A—C10—H10B	108.0
C13—N2—C10	109.04 (17)	N2—C11—C12	111.28 (18)
O1—C1—C2	113.28 (18)	N2—C11—H11A	109.4
O1—C1—H1A	108.9	C12—C11—H11A	109.4
C2—C1—H1A	108.9	N2—C11—H11B	109.4
O1—C1—H1B	108.9	C12—C11—H11B	109.4
C2—C1—H1B	108.9	H11A—C11—H11B	108.0
H1A—C1—H1B	107.7	C8—C12—C11	109.66 (18)
C3—C2—C7	116.8 (2)	C8—C12—H12A	109.7
C3—C2—C1	121.16 (19)	C11—C12—H12A	109.7
C7—C2—C1	121.99 (19)	C8—C12—H12B	109.7
C4—C3—C2	122.8 (2)	C11—C12—H12B	109.7
C4—C3—Br1	118.18 (16)	H12A—C12—H12B	108.2
C2—C3—Br1	119.04 (16)	N2—C13—C14	112.97 (18)
C5—C4—C3	118.9 (2)	N2—C13—H13A	109.0
C5—C4—H4	120.5	C14—C13—H13A	109.0
C3—C4—H4	120.5	N2—C13—H13B	109.0
C4—C5—C6	120.1 (2)	C14—C13—H13B	109.0
C4—C5—H5	119.9	H13A—C13—H13B	107.8
C6—C5—H5	119.9	C19—C14—C15	118.5 (2)
C5—C6—C7	120.0 (2)	C19—C14—C13	120.0 (2)
C5—C6—H6	120.0	C15—C14—C13	121.4 (2)
C7—C6—H6	120.0	C16—C15—C14	120.4 (2)
C6—C7—C2	121.3 (2)	C16—C15—H15	119.8
C6—C7—H7	119.4	C14—C15—H15	119.8
C2—C7—H7	119.4	C17—C16—C15	120.3 (2)
N1—C8—C9	127.48 (19)	C17—C16—H16	119.9
N1—C8—C12	117.18 (19)	C15—C16—H16	119.9
C9—C8—C12	115.27 (18)	C18—C17—C16	119.6 (2)
C8—C9—C10	109.98 (18)	C18—C17—H17	120.2
C8—C9—H9A	109.7	C16—C17—H17	120.2
C10—C9—H9A	109.7	C19—C18—C17	119.8 (2)
C8—C9—H9B	109.7	C19—C18—H18	120.1
C10—C9—H9B	109.7	C17—C18—H18	120.1
H9A—C9—H9B	108.2	C18—C19—C14	121.3 (2)
N2—C10—C9	111.39 (18)	C18—C19—H19	119.3
N2—C10—H10A	109.3	C14—C19—H19	119.3

C1—O1—N1—C8	−169.11 (18)	C13—N2—C10—C9	177.2 (2)
N1—O1—C1—C2	78.7 (2)	C8—C9—C10—N2	53.8 (3)
O1—C1—C2—C3	−175.08 (17)	C13—N2—C11—C12	−177.74 (17)
O1—C1—C2—C7	5.1 (3)	C10—N2—C11—C12	61.7 (2)
C7—C2—C3—C4	−2.5 (3)	N1—C8—C12—C11	−127.6 (2)
C1—C2—C3—C4	177.67 (19)	C9—C8—C12—C11	49.4 (3)
C7—C2—C3—Br1	175.90 (15)	N2—C11—C12—C8	−54.7 (2)
C1—C2—C3—Br1	−3.9 (3)	C11—N2—C13—C14	68.1 (3)
C2—C3—C4—C5	1.4 (3)	C10—N2—C13—C14	−170.8 (2)
Br1—C3—C4—C5	−177.08 (16)	N2—C13—C14—C19	74.1 (3)
C3—C4—C5—C6	0.7 (3)	N2—C13—C14—C15	−106.4 (3)
C4—C5—C6—C7	−1.4 (3)	C19—C14—C15—C16	0.5 (3)
C5—C6—C7—C2	0.2 (3)	C13—C14—C15—C16	−179.0 (2)
C3—C2—C7—C6	1.7 (3)	C14—C15—C16—C17	0.2 (4)
C1—C2—C7—C6	−178.5 (2)	C15—C16—C17—C18	−1.0 (4)
O1—N1—C8—C9	3.7 (3)	C16—C17—C18—C19	1.0 (4)
O1—N1—C8—C12	−179.76 (17)	C17—C18—C19—C14	−0.3 (4)
N1—C8—C9—C10	127.6 (2)	C15—C14—C19—C18	−0.5 (3)
C12—C8—C9—C10	−49.1 (3)	C13—C14—C19—C18	179.0 (2)
C11—N2—C10—C9	−61.2 (2)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁BrN₂O
M_r	373.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	21.1586 (5), 5.6731 (2), 14.6425 (4)
β (°)	103.037 (3)
V (Å³)	1712.31 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.41
Crystal size (mm)	0.40 × 0.12 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur E
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.448, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9090, 4525, 3556
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.078, 1.03
No. of reflections	4525
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.69

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR92 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database. RMF also thanks the Universidad del Valle, Colombia, and AL thanks Pontificia Universidad Javeriana, Colombia, for partial financial support.

References

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