3-Chloro-r-2,c-6-bis­(4-fluoro­phen­yl)-3-methyl­piperidin-4-one

The title compound, C₁₈H₁₆ClF₂NO, contains one independent mol­ecule in the asymmetric unit, with the piperidin-4-one ring adopting a slightly distorted chair conformation and an equatorial orientation of all the substituents except chlorine. A single weak inter­molecular C—H...O inter­action influences the crystal packing, forming infinite one-dimensional zigzag chains along the a axis. The structure was refined as a two-component inversion twin.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.049
• wR factor = 0.122
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.80 Report
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00616 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT792_ALERT_1_G The Model has Chirality at C1      (Polar  SPGR)          R Verify
PLAT792_ALERT_1_G The Model has Chirality at C2      (Polar  SPGR)          S Verify
PLAT792_ALERT_1_G The Model has Chirality at C5      (Polar  SPGR)          R Verify
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         10 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........         10 Note

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

   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-Chloro-r-2,c-6-bis(4-fluorophenyl)-3-methylpiperidin-4-one

Crystal data

C18H16ClF2NO	Dx = 1.403 Mg m^−3
Mr = 335.77	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pna21	Cell parameters from 3685 reflections
a = 6.2844 (2) Å	θ = 3.8–71.6°
b = 11.7141 (5) Å	µ = 2.35 mm^−1
c = 21.6006 (10) Å	T = 173 K
V = 1590.15 (11) Å^3	Needle, colourless
Z = 4	0.48 × 0.15 × 0.14 mm
F(000) = 696

Data collection

Rigaku Oxford Diffraction diffractometer	2341 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	2207 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 16.0416 pixels mm^-1	θmax = 71.3°, θmin = 3.8°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −14→14
Tmin = 0.441, Tmax = 1.000	l = −22→26
10608 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0862P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.56 e Å^−3
2341 reflections	Δρmin = −0.20 e Å^−3
210 parameters	Absolute structure: Flack x determined using 650 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.02 (3)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. IR (KBr): 3325.34 (N-H), 3075.55, 3008.86 (υC-H), 1716.35 (υC=O), 1609.56, 1508.41 (υC=C), 767.12 (υC-Cl) cm^-1. ¹H NMR (500 MHz, CDCl₃): δ 7.54 - 7.03 (m, Aromatic protons), 4.06 - 4.03 (dd, H(6) proton), 3.94 (s, H(2) proton ), 3.45 - 3.40 (dd, H(5e) proton), 2.53-2.49 (dd, H(5a) proton), 2.07 (s, NH proton), 1.42 (s, CH₃ proton).

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.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
Cl1	0.08854 (13)	0.40538 (7)	0.52705 (7)	0.0446 (3)
F1	0.9527 (6)	0.3396 (4)	0.23545 (15)	0.0731 (10)
F2	0.6850 (5)	0.3219 (3)	0.76478 (13)	0.0620 (8)
O1	0.0162 (5)	0.6728 (2)	0.46516 (17)	0.0479 (8)
N1	0.5435 (5)	0.4835 (3)	0.49061 (14)	0.0317 (6)
H1	0.6721	0.4620	0.4976	0.038*
C1	0.4464 (5)	0.5400 (3)	0.54363 (19)	0.0321 (7)
H1A	0.5031	0.6197	0.5451	0.038*
C2	0.2029 (5)	0.5480 (3)	0.5335 (2)	0.0347 (8)
C3	0.1544 (6)	0.6011 (3)	0.4701 (2)	0.0353 (8)
C4	0.2845 (7)	0.5591 (4)	0.4168 (2)	0.0435 (9)
H4A	0.2677	0.6123	0.3815	0.052*
H4B	0.2310	0.4834	0.4037	0.052*
C5	0.5239 (6)	0.5493 (3)	0.43340 (19)	0.0357 (8)
H5	0.5827	0.6275	0.4404	0.043*
C6	0.6454 (6)	0.4932 (4)	0.38161 (19)	0.0377 (8)
C7	0.6428 (8)	0.3745 (4)	0.3746 (2)	0.0445 (9)
H7	0.5686	0.3288	0.4038	0.053*
C8	0.7467 (9)	0.3231 (4)	0.3258 (2)	0.0520 (10)
H8	0.7455	0.2424	0.3212	0.062*
C9	0.8523 (8)	0.3909 (5)	0.2838 (2)	0.0517 (11)
C10	0.8613 (8)	0.5067 (5)	0.2891 (2)	0.0541 (11)
H10	0.9369	0.5514	0.2597	0.065*
C11	0.7571 (8)	0.5577 (4)	0.3385 (2)	0.0462 (9)
H11	0.7623	0.6383	0.3430	0.055*
C12	0.5098 (6)	0.4818 (3)	0.60302 (18)	0.0324 (7)
C13	0.5488 (7)	0.5447 (4)	0.6568 (2)	0.0397 (9)
H13	0.5356	0.6254	0.6557	0.048*
C14	0.6059 (7)	0.4923 (4)	0.7111 (2)	0.0438 (9)
H14	0.6301	0.5357	0.7475	0.053*
C15	0.6271 (7)	0.3753 (4)	0.7115 (2)	0.0447 (9)
C16	0.5943 (6)	0.3102 (4)	0.6598 (2)	0.0405 (9)
H16	0.6126	0.2297	0.6612	0.049*
C17	0.5340 (6)	0.3637 (3)	0.60545 (19)	0.0359 (8)
H17	0.5088	0.3194	0.5694	0.043*
C18	0.0902 (7)	0.6093 (5)	0.5858 (2)	0.0495 (12)
H18A	−0.0600	0.6199	0.5750	0.074*
H18B	0.1569	0.6839	0.5925	0.074*
H18C	0.1007	0.5637	0.6237	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0329 (4)	0.0338 (4)	0.0673 (6)	−0.0052 (3)	−0.0073 (4)	0.0127 (4)
F1	0.071 (2)	0.104 (3)	0.0439 (15)	0.0193 (18)	0.0142 (14)	−0.0073 (16)
F2	0.0677 (18)	0.076 (2)	0.0426 (14)	0.0096 (14)	−0.0129 (13)	0.0101 (14)
O1	0.0387 (14)	0.0370 (14)	0.068 (2)	0.0091 (12)	−0.0078 (14)	0.0069 (14)
N1	0.0281 (14)	0.0305 (14)	0.0364 (17)	0.0024 (11)	−0.0015 (11)	−0.0010 (12)
C1	0.0264 (15)	0.0243 (14)	0.046 (2)	−0.0016 (11)	−0.0007 (14)	−0.0024 (14)
C2	0.0306 (16)	0.0272 (13)	0.046 (2)	0.0017 (11)	0.0021 (16)	0.0038 (15)
C3	0.0302 (18)	0.0279 (18)	0.048 (2)	−0.0026 (13)	−0.0069 (16)	0.0062 (15)
C4	0.043 (2)	0.043 (2)	0.044 (2)	0.0059 (17)	−0.0089 (17)	0.0057 (17)
C5	0.0354 (17)	0.0298 (17)	0.042 (2)	−0.0033 (14)	−0.0013 (16)	0.0013 (15)
C6	0.0366 (18)	0.0403 (19)	0.036 (2)	−0.0017 (16)	−0.0024 (15)	0.0034 (16)
C7	0.054 (2)	0.0347 (19)	0.045 (2)	−0.0015 (17)	0.0019 (19)	0.0008 (18)
C8	0.059 (3)	0.051 (2)	0.047 (2)	0.008 (2)	0.002 (2)	−0.002 (2)
C9	0.043 (2)	0.074 (3)	0.038 (2)	0.007 (2)	−0.0007 (19)	0.000 (2)
C10	0.049 (2)	0.074 (3)	0.040 (2)	0.000 (2)	0.0026 (18)	0.015 (2)
C11	0.046 (2)	0.046 (2)	0.047 (2)	−0.0040 (17)	−0.0002 (19)	0.0101 (18)
C12	0.0256 (15)	0.0325 (16)	0.0390 (18)	−0.0012 (13)	0.0022 (13)	−0.0025 (15)
C13	0.039 (2)	0.039 (2)	0.042 (2)	0.0005 (17)	0.0014 (16)	−0.0049 (18)
C14	0.039 (2)	0.055 (3)	0.037 (2)	−0.0006 (17)	−0.0026 (16)	−0.0086 (19)
C15	0.0363 (19)	0.057 (3)	0.041 (2)	0.0039 (18)	−0.0053 (17)	0.0046 (19)
C16	0.037 (2)	0.037 (2)	0.048 (2)	0.0057 (15)	−0.0024 (16)	0.0034 (18)
C17	0.0340 (17)	0.0339 (18)	0.0397 (19)	0.0027 (14)	0.0010 (15)	−0.0049 (15)
C18	0.041 (2)	0.057 (3)	0.051 (3)	0.0173 (18)	0.0040 (19)	−0.003 (2)

Geometric parameters (Å, º)

Cl1—C2	1.824 (3)	C7—C8	1.379 (7)
F1—C9	1.360 (6)	C8—H8	0.9500
F2—C15	1.360 (5)	C8—C9	1.376 (7)
O1—C3	1.213 (5)	C9—C10	1.363 (8)
N1—H1	0.8599	C10—H10	0.9500
N1—C1	1.457 (5)	C10—C11	1.388 (7)
N1—C5	1.461 (5)	C11—H11	0.9500
C1—H1A	1.0000	C12—C13	1.397 (5)
C1—C2	1.548 (4)	C12—C17	1.392 (5)
C1—C12	1.507 (5)	C13—H13	0.9500
C2—C3	1.535 (6)	C13—C14	1.372 (7)
C2—C18	1.515 (6)	C14—H14	0.9500
C3—C4	1.495 (6)	C14—C15	1.376 (7)
C4—H4A	0.9900	C15—C16	1.368 (6)
C4—H4B	0.9900	C16—H16	0.9500
C4—C5	1.551 (5)	C16—C17	1.384 (6)
C5—H5	1.0000	C17—H17	0.9500
C5—C6	1.505 (6)	C18—H18A	0.9800
C6—C7	1.399 (6)	C18—H18B	0.9800
C6—C11	1.389 (6)	C18—H18C	0.9800
C7—H7	0.9500
C1—N1—H1	112.9	C7—C8—H8	120.6
C1—N1—C5	112.9 (3)	C9—C8—C7	118.7 (4)
C5—N1—H1	112.5	C9—C8—H8	120.6
N1—C1—H1A	107.5	F1—C9—C8	118.4 (5)
N1—C1—C2	109.3 (3)	F1—C9—C10	119.0 (5)
N1—C1—C12	110.7 (3)	C10—C9—C8	122.7 (4)
C2—C1—H1A	107.5	C9—C10—H10	120.9
C12—C1—H1A	107.5	C9—C10—C11	118.2 (4)
C12—C1—C2	114.1 (3)	C11—C10—H10	120.9
C1—C2—Cl1	110.2 (2)	C6—C11—C10	121.3 (4)
C3—C2—Cl1	103.0 (2)	C6—C11—H11	119.3
C3—C2—C1	110.3 (3)	C10—C11—H11	119.3
C18—C2—Cl1	107.9 (3)	C13—C12—C1	121.0 (3)
C18—C2—C1	112.7 (3)	C17—C12—C1	120.7 (3)
C18—C2—C3	112.4 (3)	C17—C12—C13	118.3 (4)
O1—C3—C2	120.1 (4)	C12—C13—H13	119.3
O1—C3—C4	123.4 (4)	C14—C13—C12	121.4 (4)
C4—C3—C2	116.5 (3)	C14—C13—H13	119.3
C3—C4—H4A	109.2	C13—C14—H14	120.8
C3—C4—H4B	109.2	C13—C14—C15	118.4 (4)
C3—C4—C5	112.1 (3)	C15—C14—H14	120.8
H4A—C4—H4B	107.9	F2—C15—C14	119.3 (4)
C5—C4—H4A	109.2	F2—C15—C16	118.3 (4)
C5—C4—H4B	109.2	C16—C15—C14	122.4 (4)
N1—C5—C4	108.5 (3)	C15—C16—H16	120.6
N1—C5—H5	108.9	C15—C16—C17	118.7 (4)
N1—C5—C6	110.8 (3)	C17—C16—H16	120.6
C4—C5—H5	108.9	C12—C17—H17	119.6
C6—C5—C4	110.7 (3)	C16—C17—C12	120.8 (4)
C6—C5—H5	108.9	C16—C17—H17	119.6
C7—C6—C5	120.5 (4)	C2—C18—H18A	109.5
C11—C6—C5	121.1 (4)	C2—C18—H18B	109.5
C11—C6—C7	118.3 (4)	C2—C18—H18C	109.5
C6—C7—H7	119.6	H18A—C18—H18B	109.5
C8—C7—C6	120.8 (4)	H18A—C18—H18C	109.5
C8—C7—H7	119.6	H18B—C18—H18C	109.5
Cl1—C2—C3—O1	106.0 (3)	C4—C5—C6—C11	98.1 (4)
Cl1—C2—C3—C4	−73.7 (4)	C5—N1—C1—C2	65.3 (3)
F1—C9—C10—C11	179.7 (4)	C5—N1—C1—C12	−168.2 (3)
F2—C15—C16—C17	179.6 (4)	C5—C6—C7—C8	177.4 (4)
O1—C3—C4—C5	136.3 (4)	C5—C6—C11—C10	−177.0 (4)
N1—C1—C2—Cl1	61.3 (3)	C6—C7—C8—C9	−0.3 (7)
N1—C1—C2—C3	−51.7 (3)	C7—C6—C11—C10	1.0 (7)
N1—C1—C2—C18	−178.1 (3)	C7—C8—C9—F1	−179.4 (4)
N1—C1—C12—C13	142.7 (3)	C7—C8—C9—C10	1.1 (8)
N1—C1—C12—C17	−36.4 (4)	C8—C9—C10—C11	−0.8 (7)
N1—C5—C6—C7	40.5 (5)	C9—C10—C11—C6	−0.3 (7)
N1—C5—C6—C11	−141.5 (4)	C11—C6—C7—C8	−0.7 (7)
C1—N1—C5—C4	−64.1 (4)	C12—C1—C2—Cl1	−63.2 (4)
C1—N1—C5—C6	174.3 (3)	C12—C1—C2—C3	−176.2 (3)
C1—C2—C3—O1	−136.4 (4)	C12—C1—C2—C18	57.4 (4)
C1—C2—C3—C4	43.9 (4)	C12—C13—C14—C15	0.9 (6)
C1—C12—C13—C14	179.8 (4)	C13—C12—C17—C16	0.3 (6)
C1—C12—C17—C16	179.3 (3)	C13—C14—C15—F2	179.5 (4)
C2—C1—C12—C13	−93.6 (4)	C13—C14—C15—C16	0.3 (7)
C2—C1—C12—C17	87.4 (4)	C14—C15—C16—C17	−1.1 (7)
C2—C3—C4—C5	−44.0 (4)	C15—C16—C17—C12	0.8 (6)
C3—C4—C5—N1	51.1 (4)	C17—C12—C13—C14	−1.2 (6)
C3—C4—C5—C6	172.9 (3)	C18—C2—C3—O1	−9.9 (5)
C4—C5—C6—C7	−79.9 (5)	C18—C2—C3—C4	170.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	1.00	2.44	3.328 (5)	148

Symmetry code: (i) x+1/2, −y+3/2, z.