1-Benzyl-piperidin-4-one O-(2-bromo-benz-yl)oxime.

In the title mol-ecule, C(19)H(21)BrN(2)O, 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 inter-molecular inter-actions.

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 = 373.29

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.078

S = 1.03

4525 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.69 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040263/gg2101sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040263/gg2101Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812040263/gg2101Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H21BrN2O	F(000) = 768
Mr = 373.29	Dx = 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

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

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(Fo2) + (0.0294P)2 + 0.3261P] where P = (Fo2 + 2Fc2)/3
4525 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.69 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)