r-2,c-6-Bis(4-chloro-phen-yl)-t-3-isopropyl-1-nitro-sopiperidin-4-one.

In the title mol-ecule, C(20)H(20)Cl(2)N(2)O(2), the piperidine ring adopts a chair conformation and the nitroso group at position 1 has a bis-ectional orientation. The two benzene rings and the isopropyl group attached to the piperidine ring in positions 2, 6 and 3, respectively, have axial orientations. The dihedral angle between the two benzene rings is 21.56 (13)°. One of the Cl atoms is disordered over two positions in a 0.281 (5):0.719 (5) ratio. In the crystal structure, mol-ecules are linked by C-H⋯O hydrogen bonds and a short C-H⋯O contact occurs within the mol-ecule.

Related literature

For related crystal structures, see: Balamurugan et al. (2006 ▶, 2007 ▶); Thiruvalluvar, Balamurugan, Jayabharathi & Manimekalai (2007 ▶); Thiruvalluvar, Balamurugan, Jayabharathi, Manimekalai & Rajarajan (2007 ▶).

Experimental

Crystal data

C20H20Cl2N2O2

M = 391.28

Triclinic,

a = 8.2771 (2) Å

b = 11.1921 (4) Å

c = 11.2351 (4) Å

α = 93.375 (3)°

β = 106.924 (3)°

γ = 104.549 (3)°

V = 953.95 (6) Å3

Z = 2

Cu Kα radiation

μ = 3.20 mm−1

T = 200 (2) K

0.54 × 0.47 × 0.41 mm

Data collection

Oxford Diffraction R Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.269, T max = 1.000 (expected range = 0.073–0.270)

8014 measured reflections

3752 independent reflections

3506 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.155

S = 1.02

3752 reflections

239 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029723/hb2797sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029723/hb2797Isup2.hkl

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

C20H20Cl2N2O2	Z = 2
Mr = 391.28	F(000) = 408
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Melting point: 371 K
a = 8.2771 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.1921 (4) Å	Cell parameters from 7346 reflections
c = 11.2351 (4) Å	θ = 4.1–73.2°
α = 93.375 (3)°	µ = 3.20 mm−1
β = 106.924 (3)°	T = 200 K
γ = 104.549 (3)°	Chunk, colourless
V = 953.95 (6) Å3	0.54 × 0.47 × 0.41 mm

Oxford Diffraction R Gemini diffractometer	3752 independent reflections
Radiation source: fine-focus sealed tube	3506 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 10.5081 pixels mm-1	θmax = 73.6°, θmin = 4.1°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −13→13
Tmin = 0.269, Tmax = 1.000	l = −13→13
8014 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0861P)2 + 0.6137P] where P = (Fo2 + 2Fc2)/3
3752 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.55 e Å−3
2 restraints	Δρmin = −0.43 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
Cl2	0.43589 (10)	−0.19782 (5)	0.33972 (6)	0.0590 (2)
Cl6A	−0.1316 (3)	−0.06761 (12)	0.2338 (3)	0.0841 (7)	0.719 (5)
O4	0.7087 (2)	0.46794 (17)	0.48136 (13)	0.0497 (5)
O11	0.5501 (3)	0.32189 (19)	−0.05880 (16)	0.0660 (7)
N1	0.4995 (2)	0.34969 (16)	0.11627 (14)	0.0372 (5)
N11	0.4570 (3)	0.35585 (18)	−0.00614 (17)	0.0522 (6)
C2	0.6545 (3)	0.31257 (18)	0.18850 (17)	0.0334 (5)
C3	0.7723 (3)	0.42145 (18)	0.29227 (17)	0.0327 (5)
C4	0.6642 (3)	0.45915 (17)	0.36822 (18)	0.0348 (6)
C5	0.5004 (3)	0.49030 (18)	0.29305 (18)	0.0363 (6)
C6	0.3862 (3)	0.39307 (19)	0.17854 (19)	0.0383 (6)
C13	0.8596 (3)	0.53527 (19)	0.2373 (2)	0.0389 (6)
C21	0.5990 (3)	0.18630 (18)	0.23147 (17)	0.0326 (5)
C22	0.4852 (3)	0.08611 (19)	0.14198 (19)	0.0389 (6)
C23	0.4339 (3)	−0.0315 (2)	0.1750 (2)	0.0421 (6)
C24	0.4973 (3)	−0.04937 (19)	0.2980 (2)	0.0398 (6)
C25	0.6100 (3)	0.0473 (2)	0.38825 (19)	0.0409 (6)
C26	0.6609 (3)	0.16493 (19)	0.35455 (18)	0.0384 (6)
C31	0.9944 (4)	0.5055 (3)	0.1809 (3)	0.0592 (9)
C32	0.9513 (3)	0.6478 (2)	0.3399 (3)	0.0543 (8)
C61	0.2563 (3)	0.2832 (2)	0.2041 (2)	0.0421 (6)
C62	0.2692 (3)	0.2498 (2)	0.3220 (3)	0.0524 (8)
C63	0.1510 (4)	0.1436 (3)	0.3368 (4)	0.0703 (10)
C64	0.0189 (3)	0.0718 (2)	0.2332 (4)	0.0720 (12)
C65	0.0003 (3)	0.1074 (3)	0.1156 (4)	0.0746 (12)
C66	0.1184 (3)	0.2115 (3)	0.1008 (3)	0.0593 (9)
Cl6B	−0.0853 (7)	−0.0526 (4)	0.2990 (7)	0.0841 (7)	0.281 (5)
H2	0.72236	0.30238	0.12995	0.0401*
H3	0.86751	0.39229	0.34954	0.0393*
H5A	0.53537	0.57198	0.26429	0.0435*
H5B	0.42922	0.49868	0.34856	0.0435*
H6	0.31545	0.43675	0.11767	0.0459*
H13	0.76630	0.55652	0.16987	0.0467*
H22	0.44203	0.09866	0.05694	0.0467*
H23	0.35584	−0.09911	0.11325	0.0505*
H25	0.65284	0.03391	0.47303	0.0491*
H26	0.73940	0.23186	0.41688	0.0461*
H31A	0.93640	0.43346	0.11470	0.0887*
H31B	1.08772	0.48622	0.24672	0.0887*
H31C	1.04551	0.57768	0.14499	0.0887*
H32A	0.86543	0.66784	0.37622	0.0814*
H32B	1.00279	0.71949	0.30348	0.0814*
H32C	1.04446	0.62838	0.40568	0.0814*
H62	0.35940	0.29957	0.39345	0.0629*
H63	0.16109	0.12048	0.41808	0.0844*
H65	−0.09399	0.06000	0.04494	0.0896*
H66	0.10616	0.23497	0.01945	0.0712*

	U11	U22	U33	U12	U13	U23
Cl2	0.0920 (5)	0.0271 (3)	0.0621 (4)	0.0080 (3)	0.0375 (3)	0.0087 (2)
Cl6A	0.0520 (8)	0.0412 (5)	0.157 (2)	−0.0006 (5)	0.0433 (11)	0.0067 (8)
O4	0.0592 (10)	0.0591 (10)	0.0295 (7)	0.0196 (8)	0.0111 (7)	−0.0008 (6)
O11	0.1101 (16)	0.0592 (11)	0.0380 (9)	0.0351 (11)	0.0273 (10)	0.0098 (8)
N1	0.0515 (10)	0.0316 (8)	0.0251 (7)	0.0123 (7)	0.0063 (7)	0.0056 (6)
N11	0.0833 (14)	0.0385 (10)	0.0322 (9)	0.0179 (10)	0.0137 (9)	0.0057 (7)
C2	0.0445 (10)	0.0299 (9)	0.0274 (9)	0.0122 (8)	0.0124 (8)	0.0045 (7)
C3	0.0389 (10)	0.0293 (9)	0.0299 (9)	0.0105 (8)	0.0096 (7)	0.0058 (7)
C4	0.0428 (10)	0.0264 (9)	0.0327 (10)	0.0067 (8)	0.0114 (8)	0.0017 (7)
C5	0.0441 (11)	0.0289 (9)	0.0366 (10)	0.0110 (8)	0.0137 (8)	0.0024 (8)
C6	0.0430 (11)	0.0336 (10)	0.0354 (10)	0.0143 (8)	0.0050 (8)	0.0065 (8)
C13	0.0398 (10)	0.0343 (10)	0.0422 (10)	0.0093 (8)	0.0119 (8)	0.0132 (8)
C21	0.0407 (10)	0.0282 (9)	0.0322 (9)	0.0130 (8)	0.0139 (8)	0.0038 (7)
C22	0.0481 (11)	0.0347 (10)	0.0328 (10)	0.0133 (9)	0.0101 (8)	0.0022 (8)
C23	0.0489 (12)	0.0308 (10)	0.0425 (11)	0.0083 (9)	0.0125 (9)	−0.0034 (8)
C24	0.0526 (12)	0.0266 (9)	0.0471 (11)	0.0118 (8)	0.0251 (9)	0.0070 (8)
C25	0.0570 (12)	0.0333 (10)	0.0346 (10)	0.0134 (9)	0.0164 (9)	0.0083 (8)
C26	0.0503 (11)	0.0295 (10)	0.0329 (10)	0.0093 (8)	0.0114 (8)	0.0026 (7)
C31	0.0607 (15)	0.0555 (15)	0.0714 (17)	0.0117 (12)	0.0389 (13)	0.0145 (12)
C32	0.0528 (13)	0.0332 (11)	0.0700 (16)	0.0032 (10)	0.0170 (12)	0.0066 (10)
C61	0.0360 (10)	0.0342 (10)	0.0547 (12)	0.0132 (8)	0.0095 (9)	0.0065 (9)
C62	0.0463 (12)	0.0490 (13)	0.0657 (15)	0.0140 (10)	0.0207 (11)	0.0186 (11)
C63	0.0632 (17)	0.0625 (17)	0.107 (2)	0.0285 (14)	0.0448 (17)	0.0408 (17)
C64	0.0418 (13)	0.0347 (13)	0.148 (3)	0.0124 (10)	0.0409 (17)	0.0148 (16)
C65	0.0403 (13)	0.0477 (15)	0.120 (3)	0.0057 (11)	0.0118 (15)	−0.0104 (16)
C66	0.0446 (13)	0.0496 (14)	0.0720 (17)	0.0135 (11)	0.0026 (11)	−0.0012 (12)
Cl6B	0.0520 (8)	0.0412 (5)	0.157 (2)	−0.0006 (5)	0.0433 (11)	0.0067 (8)

Cl2—C24	1.745 (2)	C62—C63	1.390 (4)
Cl6A—C64	1.737 (3)	C63—C64	1.380 (5)
Cl6B—C64	1.766 (6)	C64—C65	1.379 (6)
O4—C4	1.207 (2)	C65—C66	1.373 (5)
O11—N11	1.214 (3)	C2—H2	1.0000
N1—N11	1.327 (2)	C3—H3	1.0000
N1—C2	1.476 (3)	C5—H5A	0.9900
N1—C6	1.475 (3)	C5—H5B	0.9900
C2—C21	1.525 (3)	C6—H6	1.0000
C2—C3	1.539 (3)	C13—H13	1.0000
C3—C4	1.516 (3)	C22—H22	0.9500
C3—C13	1.555 (3)	C23—H23	0.9500
C4—C5	1.510 (3)	C25—H25	0.9500
C5—C6	1.531 (3)	C26—H26	0.9500
C6—C61	1.519 (3)	C31—H31A	0.9800
C13—C32	1.527 (3)	C31—H31B	0.9800
C13—C31	1.527 (4)	C31—H31C	0.9800
C21—C22	1.393 (3)	C32—H32A	0.9800
C21—C26	1.386 (3)	C32—H32B	0.9800
C22—C23	1.385 (3)	C32—H32C	0.9800
C23—C24	1.374 (3)	C62—H62	0.9500
C24—C25	1.372 (3)	C63—H63	0.9500
C25—C26	1.388 (3)	C65—H65	0.9500
C61—C66	1.397 (4)	C66—H66	0.9500
C61—C62	1.379 (4)
N11—N1—C2	123.99 (18)	C21—C2—H2	107.00
N11—N1—C6	114.35 (18)	C2—C3—H3	108.00
C2—N1—C6	121.50 (15)	C4—C3—H3	108.00
O11—N11—N1	115.3 (2)	C13—C3—H3	108.00
N1—C2—C3	108.06 (17)	C4—C5—H5A	109.00
N1—C2—C21	110.95 (19)	C4—C5—H5B	109.00
C3—C2—C21	116.29 (15)	C6—C5—H5A	109.00
C2—C3—C4	109.5 (2)	C6—C5—H5B	109.00
C2—C3—C13	111.85 (16)	H5A—C5—H5B	108.00
C4—C3—C13	110.24 (17)	N1—C6—H6	107.00
O4—C4—C3	122.5 (2)	C5—C6—H6	107.00
O4—C4—C5	122.1 (2)	C61—C6—H6	107.00
C3—C4—C5	115.41 (17)	C3—C13—H13	109.00
C4—C5—C6	113.82 (18)	C31—C13—H13	109.00
N1—C6—C5	109.7 (2)	C32—C13—H13	109.00
N1—C6—C61	110.74 (17)	C21—C22—H22	119.00
C5—C6—C61	115.49 (18)	C23—C22—H22	119.00
C3—C13—C31	110.9 (2)	C22—C23—H23	120.00
C3—C13—C32	110.29 (18)	C24—C23—H23	120.00
C31—C13—C32	109.0 (2)	C24—C25—H25	120.00
C2—C21—C22	118.53 (17)	C26—C25—H25	120.00
C2—C21—C26	123.28 (18)	C21—C26—H26	119.00
C22—C21—C26	118.15 (18)	C25—C26—H26	119.00
C21—C22—C23	121.07 (19)	C13—C31—H31A	109.00
C22—C23—C24	119.3 (2)	C13—C31—H31B	109.00
Cl2—C24—C23	119.49 (17)	C13—C31—H31C	109.00
Cl2—C24—C25	119.45 (16)	H31A—C31—H31B	109.00
C23—C24—C25	121.1 (2)	H31A—C31—H31C	109.00
C24—C25—C26	119.39 (19)	H31B—C31—H31C	109.00
C21—C26—C25	121.06 (19)	C13—C32—H32A	109.00
C6—C61—C62	123.8 (2)	C13—C32—H32B	109.00
C6—C61—C66	117.3 (2)	C13—C32—H32C	109.00
C62—C61—C66	118.9 (2)	H32A—C32—H32B	109.00
C61—C62—C63	120.4 (3)	H32A—C32—H32C	110.00
C62—C63—C64	119.9 (3)	H32B—C32—H32C	109.00
Cl6A—C64—C63	125.8 (3)	C61—C62—H62	120.00
Cl6A—C64—C65	114.0 (3)	C63—C62—H62	120.00
C63—C64—C65	120.2 (3)	C62—C63—H63	120.00
Cl6B—C64—C63	102.5 (4)	C64—C63—H63	120.00
Cl6B—C64—C65	137.3 (4)	C64—C65—H65	120.00
C64—C65—C66	119.9 (3)	C66—C65—H65	120.00
C61—C66—C65	120.7 (3)	C61—C66—H66	120.00
N1—C2—H2	107.00	C65—C66—H66	120.00
C3—C2—H2	107.00
C2—N1—N11—O11	3.9 (3)	C3—C4—C5—C6	48.5 (2)
C6—N1—N11—O11	179.18 (19)	C4—C5—C6—N1	−40.6 (2)
N11—N1—C2—C3	120.4 (2)	C4—C5—C6—C61	85.3 (3)
N11—N1—C2—C21	−111.1 (2)	N1—C6—C61—C62	107.0 (3)
C6—N1—C2—C3	−54.6 (2)	N1—C6—C61—C66	−71.9 (3)
C6—N1—C2—C21	73.9 (2)	C5—C6—C61—C62	−18.5 (3)
N11—N1—C6—C5	−127.96 (18)	C5—C6—C61—C66	162.8 (2)
N11—N1—C6—C61	103.4 (2)	C2—C21—C22—C23	178.3 (2)
C2—N1—C6—C5	47.5 (2)	C26—C21—C22—C23	0.5 (4)
C2—N1—C6—C61	−81.1 (2)	C2—C21—C26—C25	−178.2 (2)
N1—C2—C3—C4	53.3 (2)	C22—C21—C26—C25	−0.5 (4)
N1—C2—C3—C13	−69.2 (2)	C21—C22—C23—C24	−0.3 (4)
C21—C2—C3—C4	−72.2 (2)	C22—C23—C24—Cl2	−179.0 (2)
C21—C2—C3—C13	165.3 (2)	C22—C23—C24—C25	0.1 (4)
N1—C2—C21—C22	52.8 (3)	Cl2—C24—C25—C26	179.0 (2)
N1—C2—C21—C26	−129.5 (2)	C23—C24—C25—C26	−0.1 (4)
C3—C2—C21—C22	176.8 (2)	C24—C25—C26—C21	0.3 (4)
C3—C2—C21—C26	−5.5 (4)	C6—C61—C62—C63	−176.2 (3)
C2—C3—C4—O4	127.9 (2)	C66—C61—C62—C63	2.6 (4)
C2—C3—C4—C5	−54.5 (2)	C6—C61—C66—C65	177.0 (3)
C13—C3—C4—O4	−108.6 (2)	C62—C61—C66—C65	−1.8 (4)
C13—C3—C4—C5	68.9 (2)	C61—C62—C63—C64	−0.7 (5)
C2—C3—C13—C31	−68.1 (3)	C62—C63—C64—Cl6A	176.3 (3)
C2—C3—C13—C32	171.1 (2)	C62—C63—C64—C65	−2.2 (5)
C4—C3—C13—C31	169.8 (2)	Cl6A—C64—C65—C66	−175.6 (3)
C4—C3—C13—C32	49.0 (3)	C63—C64—C65—C66	3.0 (5)
O4—C4—C5—C6	−134.0 (2)	C64—C65—C66—C61	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O11	1.00	2.24	2.676 (2)	105
C5—H5B···O4i	0.99	2.55	3.530 (3)	171
C32—H32C···O4ii	0.98	2.59	3.532 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O11	1.00	2.24	2.676 (2)	105
C5—H5B⋯O4i	0.99	2.55	3.530 (3)	171
C32—H32C⋯O4ii	0.98	2.59	3.532 (3)	162

Symmetry codes: (i) ; (ii) .