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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604743X/sg2092sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604743X/sg2092Isup2.hkl
Contains datablock I

CCDC reference: 630459

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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No errors found in this datablock

Computing details top

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 top
Crystal data top
C17H21Cl2NO2F(000) = 720.00
Mr = 342.26Dx = 1.332 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 12897 reflections
a = 6.0819 (19) Åθ = 3.4–27.5°
b = 15.592 (6) ŵ = 0.39 mm1
c = 18.000 (7) ÅT = 296 K
β = 91.087 (14)°Chunk, colourless
V = 1706.6 (10) Å30.40 × 0.38 × 0.30 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2653 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.033
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 77
Tmin = 0.846, Tmax = 0.891k = 2020
16067 measured reflectionsl = 2323
3899 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0002Fo2 + 1.1σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.035(Δ/σ)max < 0.001
wR(F2) = 0.081Δρmax = 0.40 e Å3
S = 1.00Δρmin = 0.38 e Å3
3899 reflectionsExtinction correction: Larson (1970), equation 22
200 parametersExtinction coefficient: 99 (19)
H-atom parameters constrained
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.68479 (6)0.76493 (3)0.10189 (2)0.06015 (13)
Cl20.48196 (8)0.59715 (3)0.10808 (3)0.06684 (15)
O10.81357 (14)0.76154 (6)0.27116 (6)0.0511 (3)
O20.40086 (18)0.42260 (6)0.42018 (6)0.0551 (3)
N10.52296 (17)0.84585 (6)0.29783 (6)0.0382 (3)
C10.4654 (2)0.70992 (9)0.23036 (8)0.0343 (3)
C20.4944 (2)0.69980 (10)0.14759 (8)0.0430 (4)
C30.2884 (2)0.73858 (10)0.17517 (8)0.0433 (4)
C40.6151 (2)0.77522 (9)0.26856 (8)0.0351 (3)
C50.6647 (2)0.90897 (10)0.33574 (9)0.0431 (4)
C60.6574 (2)0.89809 (10)0.41899 (9)0.0467 (4)
C70.4232 (2)0.90356 (12)0.44573 (10)0.0581 (5)
C80.2739 (2)0.84177 (12)0.40296 (9)0.0534 (5)
C90.2920 (2)0.85334 (10)0.31959 (9)0.0449 (4)
C100.4342 (2)0.63152 (9)0.27749 (8)0.0350 (3)
C110.6072 (2)0.57389 (9)0.28734 (8)0.0399 (4)
C120.5890 (2)0.50429 (10)0.33352 (8)0.0428 (4)
C130.3989 (2)0.49165 (9)0.37316 (8)0.0422 (4)
C140.2238 (2)0.54794 (10)0.36374 (9)0.0461 (4)
C150.2427 (2)0.61681 (9)0.31551 (9)0.0426 (4)
C160.2333 (2)0.41633 (10)0.47418 (9)0.0514 (4)
C170.2832 (3)0.33829 (11)0.52048 (10)0.0650 (5)
H320.15100.70720.17110.052*
H310.26040.79930.16790.052*
H520.81450.90140.31930.052*
H510.61430.96620.32290.051*
H620.71680.84230.43220.056*
H610.74520.94250.44290.056*
H720.41910.89060.49840.070*
H710.36910.96130.43720.070*
H820.32000.78390.41540.064*
H810.12250.85000.41740.065*
H910.23690.90970.30610.054*
H920.20570.80980.29390.054*
H110.73700.58320.26200.047*
H120.70450.46550.33850.051*
H140.09500.53920.38970.055*
H150.12420.65380.30840.051*
H1620.23480.46710.50540.061*
H1610.09020.41070.44990.062*
H1730.16670.32840.55470.078*
H1710.29670.28960.48830.078*
H1720.41890.34680.54760.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0573 (2)0.0711 (3)0.0525 (2)0.0052 (2)0.0137 (2)0.0158 (2)
Cl20.0902 (3)0.0604 (2)0.0497 (2)0.0031 (2)0.0056 (2)0.0165 (2)
O10.0283 (5)0.0543 (6)0.0705 (8)0.0036 (4)0.0018 (4)0.0091 (5)
O20.0655 (6)0.0408 (6)0.0593 (7)0.0062 (5)0.0100 (5)0.0126 (5)
N10.0291 (5)0.0391 (6)0.0465 (7)0.0020 (5)0.0046 (5)0.0050 (5)
C10.0290 (6)0.0367 (7)0.0373 (7)0.0026 (5)0.0004 (5)0.0007 (6)
C20.0468 (8)0.0443 (8)0.0378 (8)0.0027 (6)0.0000 (6)0.0001 (6)
C30.0352 (7)0.0492 (9)0.0454 (8)0.0055 (6)0.0050 (6)0.0057 (7)
C40.0296 (6)0.0378 (8)0.0381 (8)0.0008 (5)0.0023 (5)0.0033 (6)
C50.0410 (8)0.0367 (8)0.0520 (9)0.0081 (6)0.0061 (7)0.0024 (7)
C60.0470 (8)0.0437 (9)0.0492 (9)0.0047 (7)0.0004 (7)0.0029 (7)
C70.0571 (9)0.0684 (12)0.0490 (10)0.0030 (8)0.0092 (8)0.0079 (8)
C80.0364 (8)0.0652 (11)0.0593 (11)0.0024 (7)0.0144 (7)0.0026 (8)
C90.0315 (7)0.0459 (9)0.0574 (10)0.0068 (6)0.0036 (6)0.0057 (7)
C100.0324 (6)0.0360 (7)0.0366 (7)0.0008 (5)0.0038 (5)0.0024 (6)
C110.0358 (7)0.0422 (8)0.0418 (8)0.0042 (6)0.0034 (6)0.0022 (6)
C120.0439 (8)0.0395 (8)0.0450 (9)0.0106 (6)0.0002 (7)0.0018 (7)
C130.0497 (8)0.0333 (7)0.0436 (8)0.0010 (6)0.0012 (7)0.0003 (6)
C140.0368 (7)0.0453 (9)0.0565 (10)0.0029 (6)0.0056 (7)0.0069 (7)
C150.0313 (7)0.0408 (8)0.0555 (10)0.0024 (6)0.0015 (6)0.0053 (7)
C160.0612 (10)0.0430 (9)0.0500 (10)0.0050 (7)0.0022 (8)0.0043 (7)
C170.0911 (13)0.0510 (11)0.0528 (11)0.0048 (9)0.0010 (9)0.0102 (8)
Geometric parameters (Å, º) top
Cl1—C21.7565 (15)C16—C171.503 (2)
Cl2—C21.7525 (16)C3—H320.970
O1—C41.2256 (15)C3—H310.970
O2—C131.3694 (17)C5—H520.970
O2—C161.4252 (19)C5—H510.970
N1—C41.3475 (17)C6—H620.970
N1—C51.4681 (18)C6—H610.970
N1—C91.4698 (17)C7—H720.970
C1—C21.512 (2)C7—H710.970
C1—C31.5181 (19)C8—H820.970
C1—C41.5216 (18)C8—H810.970
C1—C101.502 (2)C9—H910.970
C2—C31.485 (2)C9—H920.970
C5—C61.510 (2)C11—H110.930
C6—C71.515 (2)C12—H120.930
C7—C81.523 (2)C14—H140.930
C8—C91.518 (2)C15—H150.930
C10—C111.3928 (19)C16—H1620.970
C10—C151.3812 (19)C16—H1610.970
C11—C121.373 (2)C17—H1730.960
C12—C131.384 (2)C17—H1710.960
C13—C141.388 (2)C17—H1720.960
C14—C151.387 (2)
Cl1···O23.5482 (11)H61···Cl23.077
O1···C33.4120 (16)H61···Cl23.337
O1···C93.3438 (16)H61···C73.303
O1···C153.5300 (16)H61···H722.987
O2···Cl13.5482 (11)H61···H712.730
O2···C33.5253 (18)H61···H812.756
C3···O13.4120 (16)H72···Cl13.389
C3···O23.5253 (18)H72···Cl23.347
C9···O13.3438 (16)H72···C73.492
C15···O13.5300 (16)H72···H612.987
Cl1···H323.204H72···H723.550
Cl1···H723.389H72···H712.877
Cl1···H823.554H72···H1713.305
Cl1···H123.370H71···Cl23.105
Cl1···H1612.962H71···C63.399
Cl1···H1713.343H71···C73.221
Cl1···H1713.595H71···H612.730
Cl2···H523.534H71···H722.877
Cl2···H513.410H71···H712.995
Cl2···H613.077H82···Cl13.554
Cl2···H613.337H82···C173.268
Cl2···H723.347H82···H1733.490
Cl2···H713.105H82···H1713.099
Cl2···H913.575H82···H1722.660
O1···H322.883H81···O13.490
O1···H313.373H81···C53.256
O1···H813.490H81···C62.927
O1···H913.507H81···H522.673
O1···H922.527H81···H622.490
O1···H152.606H81···H612.756
O1···H1733.434H81···H1733.335
O2···H312.667H91···Cl23.575
O2···H1623.091H91···O13.507
N1···H123.521H91···C53.531
C2···H1713.303H91···C123.497
C3···H1613.589H91···C133.553
C3···H1713.082H91···H522.588
C5···H813.256H92···O12.527
C5···H913.531H92···H522.820
C5···H113.298H11···C53.298
C5···H123.367H11···C143.495
C6···H713.399H11···C153.248
C6···H812.927H11···H323.593
C6···H1713.377H11···H523.203
C7···H613.303H11···H512.556
C7···H723.492H11···H143.210
C7···H713.221H11···H152.716
C8···H523.283H12···Cl13.370
C8···H623.439H12···N13.521
C8···H1723.586H12···C53.367
C9···H523.000H12···C143.432
C10···H1723.274H12···H523.011
C11···H523.343H12···H513.126
C11···H513.123H12···H142.780
C11···H143.504H12···H1623.017
C11···H153.396H12···H1613.175
C11···H1733.485H14···C113.504
C11···H1723.225H14···C123.267
C12···H523.247H14···C163.264
C12···H513.424H14···C173.419
C12···H913.497H14···H113.210
C12···H143.267H14···H122.780
C12···H1623.105H14···H1622.782
C12···H1733.598H14···H1613.215
C12···H1723.159H14···H1732.802
C13···H313.233H15···O12.606
C13···H913.553H15···C113.396
C13···H1623.158H15···H112.716
C13···H1723.090H15···H1733.073
C14···H113.495H162···O23.091
C14···H123.432H162···C123.105
C14···H1733.412H162···C133.158
C14···H1723.136H162···C163.404
C15···H113.248H162···H123.017
C15···H1733.550H162···H142.782
C15···H1723.231H162···H1623.038
C16···H313.142H162···H1623.394
C16···H143.264H162···H1612.872
C16···H1623.404H161···Cl12.962
C17···H313.450H161···C33.589
C17···H622.941H161···H312.900
C17···H823.268H161···H123.175
C17···H143.419H161···H143.215
H32···Cl13.204H161···H1622.872
H32···O12.883H161···H1613.505
H32···H113.593H173···O13.434
H32···H1713.165H173···C113.485
H31···O13.373H173···C123.598
H31···O22.667H173···C143.412
H31···C133.233H173···C153.550
H31···C163.142H173···H622.763
H31···C173.450H173···H823.490
H31···H1612.900H173···H813.335
H31···H1712.829H173···H142.802
H52···Cl23.534H173···H153.073
H52···C83.283H171···Cl13.343
H52···C93.000H171···Cl13.595
H52···C113.343H171···C23.303
H52···C123.247H171···C33.082
H52···H812.673H171···C63.377
H52···H912.588H171···H323.165
H52···H922.820H171···H312.829
H52···H113.203H171···H622.507
H52···H123.011H171···H723.305
H51···Cl23.410H171···H823.099
H51···C113.123H172···C83.586
H51···C123.424H172···C103.274
H51···H112.556H172···C113.225
H51···H123.126H172···C123.159
H62···C83.439H172···C133.090
H62···C172.941H172···C143.136
H62···H812.490H172···C153.231
H62···H1732.763H172···H623.084
H62···H1712.507H172···H822.660
H62···H1723.084
C13—O2—C16118.52 (11)C6—C5—H52109.5
C4—N1—C5118.99 (10)C6—C5—H51109.0
C4—N1—C9125.16 (11)H52—C5—H51109.5
C5—N1—C9112.24 (11)C5—C6—H62109.0
C2—C1—C358.69 (9)C5—C6—H61109.5
C2—C1—C4115.79 (11)C7—C6—H62108.7
C2—C1—C10119.34 (12)C7—C6—H61109.4
C3—C1—C4120.64 (12)H62—C6—H61109.5
C3—C1—C10120.90 (11)C6—C7—H72109.9
C4—C1—C10111.73 (11)C6—C7—H71108.7
Cl1—C2—Cl2111.20 (8)C8—C7—H72109.7
Cl1—C2—C1119.44 (10)C8—C7—H71108.0
Cl1—C2—C3119.28 (11)H72—C7—H71109.5
Cl2—C2—C1119.36 (10)C7—C8—H82107.8
Cl2—C2—C3118.52 (10)C7—C8—H81109.9
C1—C2—C360.86 (9)C9—C8—H82108.2
C1—C3—C260.44 (9)C9—C8—H81109.7
O1—C4—N1122.95 (12)H82—C8—H81109.5
O1—C4—C1118.78 (12)N1—C9—H91109.4
N1—C4—C1118.27 (10)N1—C9—H92109.2
N1—C5—C6110.98 (12)C8—C9—H91108.9
C5—C6—C7110.77 (12)C8—C9—H92109.8
C6—C7—C8111.05 (14)H91—C9—H92109.5
C7—C8—C9111.76 (13)C10—C11—H11118.9
N1—C9—C8110.00 (11)C12—C11—H11119.9
C1—C10—C11119.59 (11)C11—C12—H12120.2
C1—C10—C15122.12 (12)C13—C12—H12119.7
C11—C10—C15118.18 (13)C13—C14—H14119.9
C10—C11—C12121.16 (13)C15—C14—H14120.5
C11—C12—C13120.17 (13)C10—C15—H15119.1
O2—C13—C12115.65 (12)C14—C15—H15119.6
O2—C13—C14124.79 (13)O2—C16—H162109.9
C12—C13—C14119.57 (13)O2—C16—H161110.2
C13—C14—C15119.59 (13)C17—C16—H162109.8
C10—C15—C14121.28 (12)C17—C16—H161110.3
O2—C16—C17107.11 (13)H162—C16—H161109.5
C1—C3—H32120.0C16—C17—H173110.0
C1—C3—H31119.8C16—C17—H171108.9
C2—C3—H32120.0C16—C17—H172109.5
C2—C3—H31119.9H173—C17—H171109.5
H32—C3—H31109.5H173—C17—H172109.5
N1—C5—H52108.9H171—C17—H172109.5
N1—C5—H51109.0
C13—O2—C16—C17176.65 (12)C4—C1—C3—C2103.39 (14)
C16—O2—C13—C12166.41 (12)C3—C1—C10—C11136.86 (13)
C16—O2—C13—C1413.2 (2)C3—C1—C10—C1547.2 (2)
C4—N1—C5—C6100.09 (15)C10—C1—C3—C2107.72 (14)
C5—N1—C4—O11.0 (2)C4—C1—C10—C1171.74 (16)
C5—N1—C4—C1179.21 (12)C4—C1—C10—C15104.24 (14)
C4—N1—C9—C899.83 (16)C10—C1—C4—O175.30 (16)
C9—N1—C4—O1157.90 (14)C10—C1—C4—N1104.95 (14)
C9—N1—C4—C122.4 (2)Cl1—C2—C3—C1109.42 (12)
C5—N1—C9—C858.36 (16)Cl2—C2—C3—C1109.63 (12)
C9—N1—C5—C659.60 (15)N1—C5—C6—C755.93 (16)
C3—C1—C2—Cl1109.17 (13)C5—C6—C7—C852.63 (18)
C3—C1—C2—Cl2108.27 (12)C6—C7—C8—C952.52 (18)
C2—C1—C4—O165.82 (17)C7—C8—C9—N154.60 (17)
C2—C1—C4—N1113.93 (14)C1—C10—C11—C12176.11 (13)
C4—C1—C2—Cl12.46 (16)C1—C10—C15—C14174.41 (13)
C4—C1—C2—Cl2140.09 (10)C11—C10—C15—C141.6 (2)
C4—C1—C2—C3111.63 (13)C15—C10—C11—C120.03 (16)
C2—C1—C10—C1167.85 (17)C10—C11—C12—C132.0 (2)
C2—C1—C10—C15116.17 (15)C11—C12—C13—O2177.13 (12)
C10—C1—C2—Cl1140.48 (10)C11—C12—C13—C142.5 (2)
C10—C1—C2—Cl22.07 (16)O2—C13—C14—C15178.67 (13)
C10—C1—C2—C3110.35 (13)C12—C13—C14—C150.9 (2)
C3—C1—C4—O1133.21 (14)C13—C14—C15—C101.2 (2)
C3—C1—C4—N146.55 (18)
 

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