2,2-Dichloro-1-(4-ethoxy­phen­yl)cyclo­propanyl piperidin-1-yl ketone

The title compound, C₁₇H₂₁Cl₂NO₂, a cyclo­propane derivative related to the insecticide cyclo­prothrin, was prepared from piperidine and 2,2-dichloro-1-(4-ethoxy­phen­yl)cyclo­propane­carbonyl chloride. The six-membered piperidine ring has a chair conformation. The orientation of the carbonyl group relative to the cyclo­propane ring may be described by the torsion angle X-C-C=O of -98.3°, where X is the centroid of the cyclo­propane ring.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.035
• wR factor = 0.081
• Data-to-parameter ratio = 19.5

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

2,2-Dichloro-1-(4-ethoxyphenyl)cyclopropanyl piperidin-1-yl ketone

Crystal data

C17H21Cl2NO2	F(000) = 720.00
Mr = 342.26	Dx = 1.332 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 12897 reflections
a = 6.0819 (19) Å	θ = 3.4–27.5°
b = 15.592 (6) Å	µ = 0.39 mm^−1
c = 18.000 (7) Å	T = 296 K
β = 91.087 (14)°	Chunk, colourless
V = 1706.6 (10) Å^3	0.40 × 0.38 × 0.30 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2653 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.033
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→7
Tmin = 0.846, Tmax = 0.891	k = −20→20
16067 measured reflections	l = −23→23
3899 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0002Fo^2 + 1.1σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max < 0.001
wR(F^2) = 0.081	Δρmax = 0.40 e Å^−3
S = 1.00	Δρmin = −0.38 e Å^−3
3899 reflections	Extinction correction: Larson (1970), equation 22
200 parameters	Extinction coefficient: 99 (19)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Cl1	0.68479 (6)	0.76493 (3)	0.10189 (2)	0.06015 (13)
Cl2	0.48196 (8)	0.59715 (3)	0.10808 (3)	0.06684 (15)
O1	0.81357 (14)	0.76154 (6)	0.27116 (6)	0.0511 (3)
O2	0.40086 (18)	0.42260 (6)	0.42018 (6)	0.0551 (3)
N1	0.52296 (17)	0.84585 (6)	0.29783 (6)	0.0382 (3)
C1	0.4654 (2)	0.70992 (9)	0.23036 (8)	0.0343 (3)
C2	0.4944 (2)	0.69980 (10)	0.14759 (8)	0.0430 (4)
C3	0.2884 (2)	0.73858 (10)	0.17517 (8)	0.0433 (4)
C4	0.6151 (2)	0.77522 (9)	0.26856 (8)	0.0351 (3)
C5	0.6647 (2)	0.90897 (10)	0.33574 (9)	0.0431 (4)
C6	0.6574 (2)	0.89809 (10)	0.41899 (9)	0.0467 (4)
C7	0.4232 (2)	0.90356 (12)	0.44573 (10)	0.0581 (5)
C8	0.2739 (2)	0.84177 (12)	0.40296 (9)	0.0534 (5)
C9	0.2920 (2)	0.85334 (10)	0.31959 (9)	0.0449 (4)
C10	0.4342 (2)	0.63152 (9)	0.27749 (8)	0.0350 (3)
C11	0.6072 (2)	0.57389 (9)	0.28734 (8)	0.0399 (4)
C12	0.5890 (2)	0.50429 (10)	0.33352 (8)	0.0428 (4)
C13	0.3989 (2)	0.49165 (9)	0.37316 (8)	0.0422 (4)
C14	0.2238 (2)	0.54794 (10)	0.36374 (9)	0.0461 (4)
C15	0.2427 (2)	0.61681 (9)	0.31551 (9)	0.0426 (4)
C16	0.2333 (2)	0.41633 (10)	0.47418 (9)	0.0514 (4)
C17	0.2832 (3)	0.33829 (11)	0.52048 (10)	0.0650 (5)
H32	0.1510	0.7072	0.1711	0.052*
H31	0.2604	0.7993	0.1679	0.052*
H52	0.8145	0.9014	0.3193	0.052*
H51	0.6143	0.9662	0.3229	0.051*
H62	0.7168	0.8423	0.4322	0.056*
H61	0.7452	0.9425	0.4429	0.056*
H72	0.4191	0.8906	0.4984	0.070*
H71	0.3691	0.9613	0.4372	0.070*
H82	0.3200	0.7839	0.4154	0.064*
H81	0.1225	0.8500	0.4174	0.065*
H91	0.2369	0.9097	0.3061	0.054*
H92	0.2057	0.8098	0.2939	0.054*
H11	0.7370	0.5832	0.2620	0.047*
H12	0.7045	0.4655	0.3385	0.051*
H14	0.0950	0.5392	0.3897	0.055*
H15	0.1242	0.6538	0.3084	0.051*
H162	0.2348	0.4671	0.5054	0.061*
H161	0.0902	0.4107	0.4499	0.062*
H173	0.1667	0.3284	0.5547	0.078*
H171	0.2967	0.2896	0.4883	0.078*
H172	0.4189	0.3468	0.5476	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0573 (2)	0.0711 (3)	0.0525 (2)	0.0052 (2)	0.0137 (2)	0.0158 (2)
Cl2	0.0902 (3)	0.0604 (2)	0.0497 (2)	0.0031 (2)	−0.0056 (2)	−0.0165 (2)
O1	0.0283 (5)	0.0543 (6)	0.0705 (8)	0.0036 (4)	−0.0018 (4)	−0.0091 (5)
O2	0.0655 (6)	0.0408 (6)	0.0593 (7)	0.0062 (5)	0.0100 (5)	0.0126 (5)
N1	0.0291 (5)	0.0391 (6)	0.0465 (7)	−0.0020 (5)	0.0046 (5)	−0.0050 (5)
C1	0.0290 (6)	0.0367 (7)	0.0373 (7)	0.0026 (5)	−0.0004 (5)	−0.0007 (6)
C2	0.0468 (8)	0.0443 (8)	0.0378 (8)	0.0027 (6)	0.0000 (6)	0.0001 (6)
C3	0.0352 (7)	0.0492 (9)	0.0454 (8)	0.0055 (6)	−0.0050 (6)	0.0057 (7)
C4	0.0296 (6)	0.0378 (8)	0.0381 (8)	−0.0008 (5)	0.0023 (5)	0.0033 (6)
C5	0.0410 (8)	0.0367 (8)	0.0520 (9)	−0.0081 (6)	0.0061 (7)	−0.0024 (7)
C6	0.0470 (8)	0.0437 (9)	0.0492 (9)	−0.0047 (7)	−0.0004 (7)	−0.0029 (7)
C7	0.0571 (9)	0.0684 (12)	0.0490 (10)	0.0030 (8)	0.0092 (8)	−0.0079 (8)
C8	0.0364 (8)	0.0652 (11)	0.0593 (11)	0.0024 (7)	0.0144 (7)	−0.0026 (8)
C9	0.0315 (7)	0.0459 (9)	0.0574 (10)	0.0068 (6)	0.0036 (6)	−0.0057 (7)
C10	0.0324 (6)	0.0360 (7)	0.0366 (7)	−0.0008 (5)	−0.0038 (5)	−0.0024 (6)
C11	0.0358 (7)	0.0422 (8)	0.0418 (8)	0.0042 (6)	0.0034 (6)	−0.0022 (6)
C12	0.0439 (8)	0.0395 (8)	0.0450 (9)	0.0106 (6)	−0.0002 (7)	−0.0018 (7)
C13	0.0497 (8)	0.0333 (7)	0.0436 (8)	−0.0010 (6)	−0.0012 (7)	0.0003 (6)
C14	0.0368 (7)	0.0453 (9)	0.0565 (10)	−0.0029 (6)	0.0056 (7)	0.0069 (7)
C15	0.0313 (7)	0.0408 (8)	0.0555 (10)	0.0024 (6)	−0.0015 (6)	0.0053 (7)
C16	0.0612 (10)	0.0430 (9)	0.0500 (10)	−0.0050 (7)	0.0022 (8)	0.0043 (7)
C17	0.0911 (13)	0.0510 (11)	0.0528 (11)	−0.0048 (9)	0.0010 (9)	0.0102 (8)

Geometric parameters (Å, º)

Cl1—C2	1.7565 (15)	C16—C17	1.503 (2)
Cl2—C2	1.7525 (16)	C3—H32	0.970
O1—C4	1.2256 (15)	C3—H31	0.970
O2—C13	1.3694 (17)	C5—H52	0.970
O2—C16	1.4252 (19)	C5—H51	0.970
N1—C4	1.3475 (17)	C6—H62	0.970
N1—C5	1.4681 (18)	C6—H61	0.970
N1—C9	1.4698 (17)	C7—H72	0.970
C1—C2	1.512 (2)	C7—H71	0.970
C1—C3	1.5181 (19)	C8—H82	0.970
C1—C4	1.5216 (18)	C8—H81	0.970
C1—C10	1.502 (2)	C9—H91	0.970
C2—C3	1.485 (2)	C9—H92	0.970
C5—C6	1.510 (2)	C11—H11	0.930
C6—C7	1.515 (2)	C12—H12	0.930
C7—C8	1.523 (2)	C14—H14	0.930
C8—C9	1.518 (2)	C15—H15	0.930
C10—C11	1.3928 (19)	C16—H162	0.970
C10—C15	1.3812 (19)	C16—H161	0.970
C11—C12	1.373 (2)	C17—H173	0.960
C12—C13	1.384 (2)	C17—H171	0.960
C13—C14	1.388 (2)	C17—H172	0.960
C14—C15	1.387 (2)
Cl1···O2	3.5482 (11)	H61···Cl2	3.077
O1···C3	3.4120 (16)	H61···Cl2	3.337
O1···C9	3.3438 (16)	H61···C7	3.303
O1···C15	3.5300 (16)	H61···H72	2.987
O2···Cl1	3.5482 (11)	H61···H71	2.730
O2···C3	3.5253 (18)	H61···H81	2.756
C3···O1	3.4120 (16)	H72···Cl1	3.389
C3···O2	3.5253 (18)	H72···Cl2	3.347
C9···O1	3.3438 (16)	H72···C7	3.492
C15···O1	3.5300 (16)	H72···H61	2.987
Cl1···H32	3.204	H72···H72	3.550
Cl1···H72	3.389	H72···H71	2.877
Cl1···H82	3.554	H72···H171	3.305
Cl1···H12	3.370	H71···Cl2	3.105
Cl1···H161	2.962	H71···C6	3.399
Cl1···H171	3.343	H71···C7	3.221
Cl1···H171	3.595	H71···H61	2.730
Cl2···H52	3.534	H71···H72	2.877
Cl2···H51	3.410	H71···H71	2.995
Cl2···H61	3.077	H82···Cl1	3.554
Cl2···H61	3.337	H82···C17	3.268
Cl2···H72	3.347	H82···H173	3.490
Cl2···H71	3.105	H82···H171	3.099
Cl2···H91	3.575	H82···H172	2.660
O1···H32	2.883	H81···O1	3.490
O1···H31	3.373	H81···C5	3.256
O1···H81	3.490	H81···C6	2.927
O1···H91	3.507	H81···H52	2.673
O1···H92	2.527	H81···H62	2.490
O1···H15	2.606	H81···H61	2.756
O1···H173	3.434	H81···H173	3.335
O2···H31	2.667	H91···Cl2	3.575
O2···H162	3.091	H91···O1	3.507
N1···H12	3.521	H91···C5	3.531
C2···H171	3.303	H91···C12	3.497
C3···H161	3.589	H91···C13	3.553
C3···H171	3.082	H91···H52	2.588
C5···H81	3.256	H92···O1	2.527
C5···H91	3.531	H92···H52	2.820
C5···H11	3.298	H11···C5	3.298
C5···H12	3.367	H11···C14	3.495
C6···H71	3.399	H11···C15	3.248
C6···H81	2.927	H11···H32	3.593
C6···H171	3.377	H11···H52	3.203
C7···H61	3.303	H11···H51	2.556
C7···H72	3.492	H11···H14	3.210
C7···H71	3.221	H11···H15	2.716
C8···H52	3.283	H12···Cl1	3.370
C8···H62	3.439	H12···N1	3.521
C8···H172	3.586	H12···C5	3.367
C9···H52	3.000	H12···C14	3.432
C10···H172	3.274	H12···H52	3.011
C11···H52	3.343	H12···H51	3.126
C11···H51	3.123	H12···H14	2.780
C11···H14	3.504	H12···H162	3.017
C11···H15	3.396	H12···H161	3.175
C11···H173	3.485	H14···C11	3.504
C11···H172	3.225	H14···C12	3.267
C12···H52	3.247	H14···C16	3.264
C12···H51	3.424	H14···C17	3.419
C12···H91	3.497	H14···H11	3.210
C12···H14	3.267	H14···H12	2.780
C12···H162	3.105	H14···H162	2.782
C12···H173	3.598	H14···H161	3.215
C12···H172	3.159	H14···H173	2.802
C13···H31	3.233	H15···O1	2.606
C13···H91	3.553	H15···C11	3.396
C13···H162	3.158	H15···H11	2.716
C13···H172	3.090	H15···H173	3.073
C14···H11	3.495	H162···O2	3.091
C14···H12	3.432	H162···C12	3.105
C14···H173	3.412	H162···C13	3.158
C14···H172	3.136	H162···C16	3.404
C15···H11	3.248	H162···H12	3.017
C15···H173	3.550	H162···H14	2.782
C15···H172	3.231	H162···H162	3.038
C16···H31	3.142	H162···H162	3.394
C16···H14	3.264	H162···H161	2.872
C16···H162	3.404	H161···Cl1	2.962
C17···H31	3.450	H161···C3	3.589
C17···H62	2.941	H161···H31	2.900
C17···H82	3.268	H161···H12	3.175
C17···H14	3.419	H161···H14	3.215
H32···Cl1	3.204	H161···H162	2.872
H32···O1	2.883	H161···H161	3.505
H32···H11	3.593	H173···O1	3.434
H32···H171	3.165	H173···C11	3.485
H31···O1	3.373	H173···C12	3.598
H31···O2	2.667	H173···C14	3.412
H31···C13	3.233	H173···C15	3.550
H31···C16	3.142	H173···H62	2.763
H31···C17	3.450	H173···H82	3.490
H31···H161	2.900	H173···H81	3.335
H31···H171	2.829	H173···H14	2.802
H52···Cl2	3.534	H173···H15	3.073
H52···C8	3.283	H171···Cl1	3.343
H52···C9	3.000	H171···Cl1	3.595
H52···C11	3.343	H171···C2	3.303
H52···C12	3.247	H171···C3	3.082
H52···H81	2.673	H171···C6	3.377
H52···H91	2.588	H171···H32	3.165
H52···H92	2.820	H171···H31	2.829
H52···H11	3.203	H171···H62	2.507
H52···H12	3.011	H171···H72	3.305
H51···Cl2	3.410	H171···H82	3.099
H51···C11	3.123	H172···C8	3.586
H51···C12	3.424	H172···C10	3.274
H51···H11	2.556	H172···C11	3.225
H51···H12	3.126	H172···C12	3.159
H62···C8	3.439	H172···C13	3.090
H62···C17	2.941	H172···C14	3.136
H62···H81	2.490	H172···C15	3.231
H62···H173	2.763	H172···H62	3.084
H62···H171	2.507	H172···H82	2.660
H62···H172	3.084
C13—O2—C16	118.52 (11)	C6—C5—H52	109.5
C4—N1—C5	118.99 (10)	C6—C5—H51	109.0
C4—N1—C9	125.16 (11)	H52—C5—H51	109.5
C5—N1—C9	112.24 (11)	C5—C6—H62	109.0
C2—C1—C3	58.69 (9)	C5—C6—H61	109.5
C2—C1—C4	115.79 (11)	C7—C6—H62	108.7
C2—C1—C10	119.34 (12)	C7—C6—H61	109.4
C3—C1—C4	120.64 (12)	H62—C6—H61	109.5
C3—C1—C10	120.90 (11)	C6—C7—H72	109.9
C4—C1—C10	111.73 (11)	C6—C7—H71	108.7
Cl1—C2—Cl2	111.20 (8)	C8—C7—H72	109.7
Cl1—C2—C1	119.44 (10)	C8—C7—H71	108.0
Cl1—C2—C3	119.28 (11)	H72—C7—H71	109.5
Cl2—C2—C1	119.36 (10)	C7—C8—H82	107.8
Cl2—C2—C3	118.52 (10)	C7—C8—H81	109.9
C1—C2—C3	60.86 (9)	C9—C8—H82	108.2
C1—C3—C2	60.44 (9)	C9—C8—H81	109.7
O1—C4—N1	122.95 (12)	H82—C8—H81	109.5
O1—C4—C1	118.78 (12)	N1—C9—H91	109.4
N1—C4—C1	118.27 (10)	N1—C9—H92	109.2
N1—C5—C6	110.98 (12)	C8—C9—H91	108.9
C5—C6—C7	110.77 (12)	C8—C9—H92	109.8
C6—C7—C8	111.05 (14)	H91—C9—H92	109.5
C7—C8—C9	111.76 (13)	C10—C11—H11	118.9
N1—C9—C8	110.00 (11)	C12—C11—H11	119.9
C1—C10—C11	119.59 (11)	C11—C12—H12	120.2
C1—C10—C15	122.12 (12)	C13—C12—H12	119.7
C11—C10—C15	118.18 (13)	C13—C14—H14	119.9
C10—C11—C12	121.16 (13)	C15—C14—H14	120.5
C11—C12—C13	120.17 (13)	C10—C15—H15	119.1
O2—C13—C12	115.65 (12)	C14—C15—H15	119.6
O2—C13—C14	124.79 (13)	O2—C16—H162	109.9
C12—C13—C14	119.57 (13)	O2—C16—H161	110.2
C13—C14—C15	119.59 (13)	C17—C16—H162	109.8
C10—C15—C14	121.28 (12)	C17—C16—H161	110.3
O2—C16—C17	107.11 (13)	H162—C16—H161	109.5
C1—C3—H32	120.0	C16—C17—H173	110.0
C1—C3—H31	119.8	C16—C17—H171	108.9
C2—C3—H32	120.0	C16—C17—H172	109.5
C2—C3—H31	119.9	H173—C17—H171	109.5
H32—C3—H31	109.5	H173—C17—H172	109.5
N1—C5—H52	108.9	H171—C17—H172	109.5
N1—C5—H51	109.0
C13—O2—C16—C17	−176.65 (12)	C4—C1—C3—C2	103.39 (14)
C16—O2—C13—C12	166.41 (12)	C3—C1—C10—C11	136.86 (13)
C16—O2—C13—C14	−13.2 (2)	C3—C1—C10—C15	−47.2 (2)
C4—N1—C5—C6	−100.09 (15)	C10—C1—C3—C2	−107.72 (14)
C5—N1—C4—O1	−1.0 (2)	C4—C1—C10—C11	−71.74 (16)
C5—N1—C4—C1	179.21 (12)	C4—C1—C10—C15	104.24 (14)
C4—N1—C9—C8	99.83 (16)	C10—C1—C4—O1	75.30 (16)
C9—N1—C4—O1	−157.90 (14)	C10—C1—C4—N1	−104.95 (14)
C9—N1—C4—C1	22.4 (2)	Cl1—C2—C3—C1	−109.42 (12)
C5—N1—C9—C8	−58.36 (16)	Cl2—C2—C3—C1	109.63 (12)
C9—N1—C5—C6	59.60 (15)	N1—C5—C6—C7	−55.93 (16)
C3—C1—C2—Cl1	109.17 (13)	C5—C6—C7—C8	52.63 (18)
C3—C1—C2—Cl2	−108.27 (12)	C6—C7—C8—C9	−52.52 (18)
C2—C1—C4—O1	−65.82 (17)	C7—C8—C9—N1	54.60 (17)
C2—C1—C4—N1	113.93 (14)	C1—C10—C11—C12	176.11 (13)
C4—C1—C2—Cl1	−2.46 (16)	C1—C10—C15—C14	−174.41 (13)
C4—C1—C2—Cl2	140.09 (10)	C11—C10—C15—C14	1.6 (2)
C4—C1—C2—C3	−111.63 (13)	C15—C10—C11—C12	−0.03 (16)
C2—C1—C10—C11	67.85 (17)	C10—C11—C12—C13	−2.0 (2)
C2—C1—C10—C15	−116.17 (15)	C11—C12—C13—O2	−177.13 (12)
C10—C1—C2—Cl1	−140.48 (10)	C11—C12—C13—C14	2.5 (2)
C10—C1—C2—Cl2	2.07 (16)	O2—C13—C14—C15	178.67 (13)
C10—C1—C2—C3	110.35 (13)	C12—C13—C14—C15	−0.9 (2)
C3—C1—C4—O1	−133.21 (14)	C13—C14—C15—C10	−1.2 (2)
C3—C1—C4—N1	46.55 (18)