t-3-Benzyl-r-2,c-6-di­phenyl­piperidin-4-one oxime

In the title compound, C₂₄H₂₄N₂O [systematic name: (E)-3-benzyl-2,6-di­phenyl­piperidin-4-one oxime], the piperidine ring adopts a slightly distorted chair conformation and the phenyl rings and the benzyl group substituents are attached equatorially. The oxime group makes a dihedral angle of 42.88 (12)° with the piperidine ring. The dihedral angle between the phenyl rings is 71.96 (8)°. The benzyl ring makes dihedral angles of 63.01 (8) and 59.35 (8)° with the two phenyl rings. In the crystal, mol­ecules are linked by O—H...N hydrogen bonds, forming C(7) chains along the c axis. The chains are linked by C—H...π inter­actions, forming slabs lying parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.124
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1     --  H1N    ...     Please Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.597         27 Report

Alert level G
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C2      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C5      (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          72 % Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-Benzyl-2,6-diphenylpiperidin-4-one oxime

Crystal data

C24H24N2O	F(000) = 760
Mr = 356.45	Dx = 1.213 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 19.5024 (9) Å	Cell parameters from 9891 reflections
b = 8.7503 (4) Å	θ = 2.3–66.7°
c = 11.6500 (6) Å	µ = 0.58 mm^−1
β = 100.846 (2)°	T = 296 K
V = 1952.58 (16) Å^3	Plate, colourless
Z = 4	0.22 × 0.10 × 0.04 mm

Data collection

Bruker Kappa APEX3 CCD area detector diffractometer	3448 independent reflections
Radiation source: Incoatec Microfocus Source, Bruker Kappa Duo APEX3	2981 reflections with I > 2σ(I)
Multilayer Mirror monochromator	Rint = 0.055
Detector resolution: 8.3333 pixels mm^-1	θmax = 66.9°, θmin = 2.3°
φ and ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −10→10
Tmin = 0.75, Tmax = 0.98	l = −12→13
29419 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0692P)^2 + 0.371P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3448 reflections	Δρmax = 0.16 e Å^−3
252 parameters	Δρmin = −0.22 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.71287 (6)	0.48150 (14)	0.53698 (11)	0.0344 (3)
H1	0.696340	0.448499	0.607433	0.041*
C2	0.75685 (6)	0.62853 (14)	0.56741 (11)	0.0351 (3)
H2	0.774300	0.660421	0.497550	0.042*
C3	0.70827 (6)	0.75152 (14)	0.59598 (11)	0.0355 (3)
C4	0.64540 (7)	0.77889 (15)	0.50245 (12)	0.0395 (3)
H4A	0.659495	0.809454	0.430283	0.047*
H4B	0.616634	0.859130	0.525988	0.047*
C5	0.60474 (6)	0.62797 (15)	0.48523 (11)	0.0364 (3)
H5	0.596166	0.595063	0.561691	0.044*
C6	0.75469 (6)	0.35187 (14)	0.49844 (11)	0.0362 (3)
C7	0.76226 (7)	0.21623 (16)	0.56053 (13)	0.0454 (3)
H7	0.739392	0.203561	0.623105	0.054*
C8	0.80339 (9)	0.09896 (17)	0.53092 (16)	0.0569 (4)
H8	0.808004	0.008403	0.573471	0.068*
C9	0.83739 (9)	0.11667 (19)	0.43848 (16)	0.0585 (4)
H9	0.865520	0.038605	0.419148	0.070*
C10	0.82978 (9)	0.2496 (2)	0.37481 (14)	0.0564 (4)
H10	0.852402	0.260936	0.311817	0.068*
C11	0.78851 (8)	0.36688 (17)	0.40403 (13)	0.0467 (3)
H11	0.783376	0.456359	0.360170	0.056*
C12	0.81996 (7)	0.59761 (15)	0.66502 (13)	0.0424 (3)
H12A	0.804277	0.595180	0.739226	0.051*
H12B	0.838663	0.497506	0.652662	0.051*
C13	0.87751 (7)	0.71372 (15)	0.67239 (12)	0.0398 (3)
C14	0.91929 (8)	0.7167 (2)	0.58864 (14)	0.0532 (4)
H14	0.911404	0.646502	0.527649	0.064*
C15	0.97260 (9)	0.8224 (3)	0.59409 (18)	0.0722 (5)
H15	0.999760	0.823739	0.536488	0.087*
C16	0.98532 (10)	0.9249 (2)	0.6844 (2)	0.0799 (6)
H16	1.020921	0.996431	0.688086	0.096*
C17	0.94536 (10)	0.9215 (2)	0.7691 (2)	0.0768 (6)
H17	0.954393	0.989848	0.831266	0.092*
C18	0.89179 (8)	0.81725 (19)	0.76293 (15)	0.0568 (4)
H18	0.864818	0.816768	0.820813	0.068*
C19	0.53459 (6)	0.64409 (15)	0.40399 (12)	0.0378 (3)
C20	0.48520 (7)	0.73866 (17)	0.43985 (15)	0.0487 (4)
H20	0.496318	0.789015	0.511231	0.058*
C21	0.41999 (8)	0.75889 (19)	0.37115 (17)	0.0587 (4)
H21	0.388035	0.824205	0.395815	0.070*
C22	0.40208 (8)	0.6831 (2)	0.26665 (16)	0.0588 (5)
H22	0.358067	0.696256	0.220566	0.071*
C23	0.45010 (8)	0.5872 (2)	0.23073 (15)	0.0592 (4)
H23	0.438208	0.534715	0.160376	0.071*
C24	0.51617 (7)	0.56853 (18)	0.29906 (13)	0.0488 (4)
H24	0.548246	0.504319	0.273591	0.059*
N1	0.65090 (5)	0.51402 (12)	0.44530 (9)	0.0347 (3)
N2	0.71857 (6)	0.80763 (13)	0.69892 (10)	0.0409 (3)
O1	0.66591 (5)	0.91461 (13)	0.71101 (10)	0.0533 (3)
H1N	0.6278 (8)	0.4224 (18)	0.4301 (13)	0.045 (4)*
H1O	0.6709 (10)	0.935 (2)	0.7877 (19)	0.068 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0352 (6)	0.0339 (6)	0.0355 (7)	0.0025 (5)	0.0100 (5)	0.0046 (5)
C2	0.0354 (6)	0.0349 (7)	0.0352 (7)	0.0010 (5)	0.0072 (5)	0.0033 (5)
C3	0.0363 (7)	0.0318 (6)	0.0384 (7)	−0.0014 (5)	0.0071 (5)	0.0017 (5)
C4	0.0426 (7)	0.0343 (7)	0.0399 (7)	0.0059 (5)	0.0037 (6)	−0.0002 (5)
C5	0.0362 (7)	0.0381 (7)	0.0361 (7)	0.0048 (5)	0.0094 (5)	0.0017 (5)
C6	0.0331 (6)	0.0345 (7)	0.0401 (7)	0.0018 (5)	0.0047 (5)	−0.0006 (5)
C7	0.0432 (7)	0.0397 (7)	0.0539 (9)	0.0009 (6)	0.0107 (6)	0.0066 (6)
C8	0.0567 (9)	0.0356 (8)	0.0759 (11)	0.0088 (7)	0.0059 (8)	0.0047 (7)
C9	0.0549 (9)	0.0518 (9)	0.0664 (11)	0.0185 (7)	0.0051 (8)	−0.0131 (8)
C10	0.0565 (9)	0.0677 (10)	0.0477 (9)	0.0158 (8)	0.0163 (7)	−0.0063 (7)
C11	0.0500 (8)	0.0472 (8)	0.0446 (8)	0.0101 (6)	0.0135 (6)	0.0042 (6)
C12	0.0406 (7)	0.0395 (7)	0.0448 (8)	0.0042 (6)	0.0024 (6)	0.0049 (6)
C13	0.0341 (6)	0.0404 (7)	0.0420 (7)	0.0057 (5)	−0.0005 (5)	0.0027 (6)
C14	0.0448 (8)	0.0654 (10)	0.0484 (9)	0.0013 (7)	0.0058 (6)	−0.0032 (7)
C15	0.0468 (9)	0.0985 (15)	0.0727 (12)	−0.0091 (9)	0.0145 (8)	0.0130 (11)
C16	0.0558 (11)	0.0794 (14)	0.0983 (16)	−0.0246 (10)	−0.0016 (10)	0.0029 (11)
C17	0.0664 (11)	0.0716 (13)	0.0866 (14)	−0.0156 (9)	−0.0009 (10)	−0.0255 (10)
C18	0.0509 (9)	0.0639 (10)	0.0542 (9)	−0.0015 (7)	0.0063 (7)	−0.0130 (8)
C19	0.0339 (6)	0.0382 (7)	0.0426 (7)	0.0004 (5)	0.0103 (5)	0.0046 (5)
C20	0.0393 (7)	0.0477 (8)	0.0606 (9)	0.0049 (6)	0.0131 (7)	−0.0003 (7)
C21	0.0361 (8)	0.0526 (9)	0.0886 (13)	0.0075 (7)	0.0153 (8)	0.0151 (8)
C22	0.0329 (7)	0.0702 (11)	0.0708 (11)	−0.0039 (7)	0.0033 (7)	0.0277 (9)
C23	0.0457 (8)	0.0794 (12)	0.0497 (9)	−0.0137 (8)	0.0020 (7)	0.0041 (8)
C24	0.0376 (7)	0.0600 (9)	0.0489 (9)	−0.0021 (6)	0.0083 (6)	−0.0036 (7)
N1	0.0317 (5)	0.0329 (6)	0.0400 (6)	0.0009 (4)	0.0080 (4)	−0.0011 (4)
N2	0.0379 (6)	0.0413 (6)	0.0437 (7)	0.0039 (5)	0.0081 (5)	−0.0019 (5)
O1	0.0510 (6)	0.0622 (7)	0.0456 (6)	0.0185 (5)	0.0067 (5)	−0.0107 (5)

Geometric parameters (Å, º)

C1—N1	1.4820 (16)	C12—H12A	0.9700
C1—C6	1.5138 (17)	C12—H12B	0.9700
C1—C2	1.5499 (17)	C13—C18	1.379 (2)
C1—H1	0.9800	C13—C14	1.384 (2)
C2—C3	1.5116 (17)	C14—C15	1.384 (2)
C2—C12	1.5344 (18)	C14—H14	0.9300
C2—H2	0.9800	C15—C16	1.369 (3)
C3—N2	1.2764 (17)	C15—H15	0.9300
C3—C4	1.4984 (18)	C16—C17	1.369 (3)
C4—C5	1.5340 (18)	C16—H16	0.9300
C4—H4A	0.9700	C17—C18	1.378 (3)
C4—H4B	0.9700	C17—H17	0.9300
C5—N1	1.4760 (16)	C18—H18	0.9300
C5—C19	1.5165 (18)	C19—C24	1.377 (2)
C5—H5	0.9800	C19—C20	1.3924 (19)
C6—C7	1.3833 (19)	C20—C21	1.381 (2)
C6—C11	1.3910 (19)	C20—H20	0.9300
C7—C8	1.385 (2)	C21—C22	1.373 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.375 (3)	C22—C23	1.380 (3)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.372 (2)	C23—C24	1.391 (2)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.386 (2)	C24—H24	0.9300
C10—H10	0.9300	N1—H1N	0.920 (16)
C11—H11	0.9300	N2—O1	1.4161 (14)
C12—C13	1.5044 (19)	O1—H1O	0.90 (2)
N1—C1—C6	110.00 (10)	C13—C12—H12A	108.7
N1—C1—C2	110.28 (10)	C2—C12—H12A	108.7
C6—C1—C2	112.58 (10)	C13—C12—H12B	108.7
N1—C1—H1	107.9	C2—C12—H12B	108.7
C6—C1—H1	107.9	H12A—C12—H12B	107.6
C2—C1—H1	107.9	C18—C13—C14	117.77 (14)
C3—C2—C12	114.26 (11)	C18—C13—C12	121.91 (13)
C3—C2—C1	107.37 (10)	C14—C13—C12	120.30 (13)
C12—C2—C1	110.81 (10)	C15—C14—C13	121.14 (16)
C3—C2—H2	108.1	C15—C14—H14	119.4
C12—C2—H2	108.1	C13—C14—H14	119.4
C1—C2—H2	108.1	C16—C15—C14	119.93 (18)
N2—C3—C4	125.76 (12)	C16—C15—H15	120.0
N2—C3—C2	119.10 (11)	C14—C15—H15	120.0
C4—C3—C2	114.50 (11)	C17—C16—C15	119.65 (18)
C3—C4—C5	106.84 (10)	C17—C16—H16	120.2
C3—C4—H4A	110.4	C15—C16—H16	120.2
C5—C4—H4A	110.4	C16—C17—C18	120.36 (18)
C3—C4—H4B	110.4	C16—C17—H17	119.8
C5—C4—H4B	110.4	C18—C17—H17	119.8
H4A—C4—H4B	108.6	C17—C18—C13	121.13 (16)
N1—C5—C19	113.47 (11)	C17—C18—H18	119.4
N1—C5—C4	106.96 (10)	C13—C18—H18	119.4
C19—C5—C4	112.64 (10)	C24—C19—C20	118.17 (13)
N1—C5—H5	107.8	C24—C19—C5	124.30 (12)
C19—C5—H5	107.8	C20—C19—C5	117.50 (12)
C4—C5—H5	107.8	C21—C20—C19	121.07 (15)
C7—C6—C11	118.34 (12)	C21—C20—H20	119.5
C7—C6—C1	119.88 (12)	C19—C20—H20	119.5
C11—C6—C1	121.73 (12)	C22—C21—C20	120.34 (15)
C6—C7—C8	121.00 (14)	C22—C21—H21	119.8
C6—C7—H7	119.5	C20—C21—H21	119.8
C8—C7—H7	119.5	C21—C22—C23	119.27 (14)
C9—C8—C7	119.90 (14)	C21—C22—H22	120.4
C9—C8—H8	120.1	C23—C22—H22	120.4
C7—C8—H8	120.1	C22—C23—C24	120.42 (16)
C10—C9—C8	119.98 (14)	C22—C23—H23	119.8
C10—C9—H9	120.0	C24—C23—H23	119.8
C8—C9—H9	120.0	C19—C24—C23	120.71 (15)
C9—C10—C11	120.24 (15)	C19—C24—H24	119.6
C9—C10—H10	119.9	C23—C24—H24	119.6
C11—C10—H10	119.9	C5—N1—C1	111.44 (10)
C10—C11—C6	120.53 (14)	C5—N1—H1N	110.1 (9)
C10—C11—H11	119.7	C1—N1—H1N	106.0 (10)
C6—C11—H11	119.7	C3—N2—O1	111.03 (11)
C13—C12—C2	114.15 (11)	N2—O1—H1O	106.4 (12)
N1—C1—C2—C3	52.80 (13)	C2—C12—C13—C14	−72.61 (16)
C6—C1—C2—C3	176.06 (10)	C18—C13—C14—C15	−1.5 (2)
N1—C1—C2—C12	178.22 (10)	C12—C13—C14—C15	−179.83 (14)
C6—C1—C2—C12	−58.53 (14)	C13—C14—C15—C16	0.9 (3)
C12—C2—C3—N2	−6.87 (17)	C14—C15—C16—C17	0.4 (3)
C1—C2—C3—N2	116.46 (13)	C15—C16—C17—C18	−1.1 (3)
C12—C2—C3—C4	−178.23 (11)	C16—C17—C18—C13	0.5 (3)
C1—C2—C3—C4	−54.90 (14)	C14—C13—C18—C17	0.7 (2)
N2—C3—C4—C5	−110.41 (14)	C12—C13—C18—C17	179.09 (16)
C2—C3—C4—C5	60.28 (14)	N1—C5—C19—C24	−3.99 (18)
C3—C4—C5—N1	−62.16 (13)	C4—C5—C19—C24	117.73 (14)
C3—C4—C5—C19	172.50 (10)	N1—C5—C19—C20	174.28 (12)
N1—C1—C6—C7	−116.50 (13)	C4—C5—C19—C20	−64.00 (15)
C2—C1—C6—C7	120.09 (13)	C24—C19—C20—C21	−1.3 (2)
N1—C1—C6—C11	66.07 (15)	C5—C19—C20—C21	−179.72 (13)
C2—C1—C6—C11	−57.35 (16)	C19—C20—C21—C22	1.4 (2)
C11—C6—C7—C8	1.1 (2)	C20—C21—C22—C23	−0.4 (2)
C1—C6—C7—C8	−176.45 (13)	C21—C22—C23—C24	−0.6 (2)
C6—C7—C8—C9	0.0 (2)	C20—C19—C24—C23	0.4 (2)
C7—C8—C9—C10	−0.9 (3)	C5—C19—C24—C23	178.62 (13)
C8—C9—C10—C11	0.7 (3)	C22—C23—C24—C19	0.6 (2)
C9—C10—C11—C6	0.4 (2)	C19—C5—N1—C1	−169.51 (10)
C7—C6—C11—C10	−1.3 (2)	C4—C5—N1—C1	65.66 (13)
C1—C6—C11—C10	176.22 (13)	C6—C1—N1—C5	173.66 (10)
C3—C2—C12—C13	−78.23 (14)	C2—C1—N1—C5	−61.59 (13)
C1—C2—C12—C13	160.32 (11)	C4—C3—N2—O1	−6.48 (18)
C2—C12—C13—C18	109.09 (16)	C2—C3—N2—O1	−176.78 (10)

Hydrogen-bond geometry (Å, º)

Cg3 and Cg4 are the centroids of the C13–C18 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1^i	0.90 (2)	2.00 (2)	2.8682 (16)	163 (2)
C5—H5···Cg4^ii	0.98	2.95	3.7424 (14)	139
C8—H8···Cg3^iii	0.93	2.99	3.6890 (18)	133

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.