Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C19H25Cl2NO2, the piperidine ring shows a normal chair conformation and the cyclo­propane ring forms a dihedral angle of 55.68 (17)° with the benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602811X/xu2084sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602811X/xu2084Isup2.hkl
Contains datablock I

CCDC reference: 619034

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.085
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.63 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C4 .. 5.67 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C15 .. 5.13 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 4133 Count of symmetry unique reflns 2244 Completeness (_total/calc) 184.18% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1889 Fraction of Friedel pairs measured 0.842 Are heavy atom types Z>Si present yes PLAT792_ALERT_1_G Check the Absolute Configuration of C1 = ... S PLAT792_ALERT_1_G Check the Absolute Configuration of C5 = ... S PLAT792_ALERT_1_G Check the Absolute Configuration of C6 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

2,2-Dichloro-1-(4-ethoxyphenyl)cyclopropanyl 2,3-dimethylpiperidin-1-yl ketone top
Crystal data top
C19H25Cl2NO2F(000) = 784.0
Mr = 370.32Dx = 1.258 Mg m3
Monoclinic, CcMelting point: 432-434 K K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71075 Å
a = 11.662 (5) ÅCell parameters from 8522 reflections
b = 16.242 (8) Åθ = 3.2–27.5°
c = 11.398 (5) ŵ = 0.34 mm1
β = 115.078 (19)°T = 298 K
V = 1955.3 (15) Å3Chunk, colorless
Z = 40.33 × 0.30 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3347 reflections with F2 > 2σ(F2)
Detector resolution: 10.0 pixels mm-1Rint = 0.024
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1415
Tmin = 0.888, Tmax = 0.934k = 2121
9469 measured reflectionsl = 1414
4133 independent reflections
Refinement top
Refinement on F2(Δ/σ)max < 0.001
R[F2 > 2σ(F2)] = 0.034Δρmax = 0.32 e Å3
wR(F2) = 0.085Δρmin = 0.37 e Å3
S = 1.02Extinction correction: Larson (1970), equation 22
4133 reflectionsExtinction coefficient: 145 (16)
219 parametersAbsolute structure: Flack (1983), 1889 Friedel Pairs
H-atom parameters constrainedAbsolute structure parameter: 0.009 (4)
w = 1/[0.0004Fo2 + 1σ(Fo2)]/(4Fo2)
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
Cl10.16170 (6)0.41375 (4)0.32210 (8)0.0761 (2)
Cl20.16421 (6)0.41874 (4)0.06979 (6)0.0758 (2)
O10.08258 (12)0.23702 (11)0.01319 (16)0.0682 (4)
O20.10888 (16)0.08052 (12)0.56676 (18)0.0812 (5)
N10.27535 (13)0.17874 (11)0.07917 (16)0.0496 (4)
C10.23125 (14)0.27401 (11)0.22310 (18)0.0417 (4)
C20.34566 (17)0.33123 (11)0.2730 (2)0.0454 (5)
C30.21612 (17)0.36614 (12)0.2171 (2)0.0493 (5)
C40.19111 (16)0.22899 (12)0.0953 (2)0.0471 (5)
C50.40104 (17)0.15575 (12)0.1801 (2)0.0478 (5)
C60.5000 (2)0.17168 (13)0.1271 (2)0.0605 (6)
C70.4654 (2)0.1262 (2)0.0004 (2)0.0838 (9)
C80.3332 (2)0.1458 (2)0.0964 (2)0.0871 (9)
C90.2363 (2)0.13407 (17)0.0436 (2)0.0700 (7)
C100.19811 (16)0.22639 (11)0.31800 (18)0.0410 (4)
C110.28973 (17)0.19576 (13)0.4321 (2)0.0520 (5)
C120.25725 (19)0.14796 (16)0.5127 (2)0.0619 (6)
C130.1316 (2)0.13020 (12)0.4811 (2)0.0565 (6)
C140.03855 (18)0.16178 (13)0.3695 (2)0.0567 (6)
C150.07271 (17)0.20922 (12)0.2885 (2)0.0505 (5)
C160.0141 (2)0.04778 (17)0.5293 (2)0.0796 (9)
C170.0076 (3)0.0121 (2)0.6285 (3)0.1073 (12)
C180.3989 (2)0.06890 (13)0.2284 (2)0.0656 (7)
C190.6334 (2)0.15331 (18)0.2252 (3)0.0821 (8)
H50.41990.19310.25350.057*
H60.49660.23060.10770.073*
H110.37450.20760.45470.062*
H120.32010.12740.58900.074*
H140.04630.15140.34870.068*
H150.00980.23000.21240.061*
H210.39820.33600.22630.055*
H220.39830.33550.36530.055*
H710.47210.06740.01610.101*
H720.52390.14210.03650.101*
H810.31170.11020.17100.105*
H820.33070.20280.12290.105*
H910.22860.07590.02910.084*
H920.15520.15500.10540.084*
H1610.04190.02070.44590.095*
H1620.07280.09150.52360.095*
H1710.09130.03120.61040.129*
H1720.02860.01380.71210.129*
H1730.04420.05780.62780.129*
H1810.33200.06420.25600.079*
H1820.47850.05720.30000.079*
H1830.38490.03040.15970.079*
H1910.65250.18560.30170.098*
H1920.64060.09590.24710.098*
H1930.69190.16670.18900.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0991 (4)0.0538 (3)0.0995 (5)0.0197 (2)0.0654 (4)0.0008 (3)
Cl20.0770 (3)0.0750 (4)0.0733 (4)0.0235 (3)0.0299 (3)0.0331 (3)
O10.0336 (6)0.0980 (12)0.0572 (9)0.0115 (7)0.0038 (6)0.0132 (8)
O20.0746 (11)0.0917 (12)0.0785 (11)0.0144 (9)0.0336 (9)0.0262 (9)
N10.0416 (8)0.0587 (10)0.0420 (9)0.0091 (7)0.0114 (7)0.0051 (7)
C10.0315 (7)0.0429 (9)0.0500 (10)0.0072 (6)0.0166 (7)0.0035 (8)
C20.0392 (9)0.0411 (10)0.0529 (11)0.0033 (7)0.0166 (8)0.0022 (8)
C30.0485 (10)0.0454 (10)0.0569 (11)0.0142 (8)0.0252 (9)0.0106 (9)
C40.0363 (9)0.0505 (11)0.0522 (12)0.0040 (7)0.0165 (9)0.0002 (8)
C50.0380 (8)0.0455 (10)0.0541 (11)0.0090 (7)0.0138 (8)0.0018 (8)
C60.0529 (11)0.0543 (12)0.0824 (16)0.0099 (9)0.0365 (11)0.0016 (10)
C70.0851 (17)0.100 (2)0.0843 (18)0.0258 (15)0.0532 (15)0.0009 (15)
C80.1031 (19)0.107 (2)0.0574 (15)0.0320 (17)0.0403 (15)0.0032 (14)
C90.0661 (14)0.0830 (18)0.0496 (13)0.0167 (12)0.0135 (11)0.0164 (11)
C100.0368 (8)0.0388 (9)0.0461 (10)0.0003 (7)0.0163 (8)0.0015 (7)
C110.0371 (9)0.0607 (12)0.0525 (12)0.0038 (8)0.0136 (8)0.0067 (9)
C120.0519 (11)0.0745 (15)0.0508 (13)0.0036 (10)0.0136 (10)0.0125 (10)
C130.0596 (12)0.0534 (12)0.0607 (13)0.0061 (10)0.0295 (10)0.0044 (10)
C140.0427 (10)0.0612 (13)0.0701 (15)0.0024 (9)0.0276 (10)0.0034 (10)
C150.0393 (9)0.0558 (12)0.0519 (11)0.0086 (8)0.0148 (8)0.0076 (9)
C160.0731 (15)0.0769 (17)0.103 (2)0.0048 (13)0.0512 (15)0.0194 (16)
C170.103 (2)0.098 (2)0.141 (2)0.0088 (17)0.070 (2)0.034 (2)
C180.0659 (13)0.0529 (13)0.0722 (15)0.0062 (10)0.0237 (11)0.0040 (10)
C190.0538 (12)0.0837 (18)0.112 (2)0.0081 (12)0.0384 (13)0.0035 (16)
Geometric parameters (Å, º) top
Cl1—C31.754 (2)C2—H210.970
Cl2—C31.748 (2)C2—H220.970
O1—C41.2208 (19)C5—H50.980
O2—C131.377 (3)C6—H60.980
O2—C161.415 (3)C7—H710.970
N1—C41.348 (2)C7—H720.970
N1—C51.477 (2)C8—H810.970
N1—C91.467 (3)C8—H820.970
C1—C21.524 (2)C9—H910.970
C1—C31.505 (2)C9—H920.970
C1—C41.516 (2)C11—H110.930
C1—C101.507 (3)C12—H120.930
C2—C31.481 (2)C14—H140.930
C5—C61.534 (3)C15—H150.930
C5—C181.518 (3)C16—H1610.970
C6—C71.525 (4)C16—H1620.970
C6—C191.512 (2)C17—H1710.960
C7—C81.498 (3)C17—H1720.960
C8—C91.501 (4)C17—H1730.960
C10—C111.379 (2)C18—H1810.960
C10—C151.383 (2)C18—H1820.960
C11—C121.373 (3)C18—H1830.960
C12—C131.383 (3)C19—H1910.960
C13—C141.374 (2)C19—H1920.960
C14—C151.385 (3)C19—H1930.960
C16—C171.468 (5)
C13—O2—C16118.79 (18)C7—C6—H6106.8
C4—N1—C5125.94 (17)C19—C6—H6106.8
C4—N1—C9118.67 (15)C6—C7—H71109.0
C5—N1—C9114.97 (18)C6—C7—H72109.0
C2—C1—C358.53 (11)C8—C7—H71109.0
C2—C1—C4121.16 (19)C8—C7—H72109.0
C2—C1—C10119.68 (15)H71—C7—H72109.5
C3—C1—C4116.97 (16)C7—C8—H81108.5
C3—C1—C10118.82 (18)C7—C8—H82108.5
C4—C1—C10111.93 (15)C9—C8—H81108.5
C1—C2—C360.07 (12)C9—C8—H82108.5
Cl1—C3—Cl2111.21 (10)H81—C8—H82109.5
Cl1—C3—C1118.48 (17)N1—C9—H91109.4
Cl1—C3—C2118.26 (14)N1—C9—H92109.4
Cl2—C3—C1121.06 (15)C8—C9—H91109.4
Cl2—C3—C2118.37 (18)C8—C9—H92109.4
C1—C3—C261.39 (11)H91—C9—H92109.5
O1—C4—N1122.60 (19)C10—C11—H11119.6
O1—C4—C1118.85 (19)C12—C11—H11119.6
N1—C4—C1118.48 (13)C11—C12—H12119.8
N1—C5—C6108.33 (17)C13—C12—H12119.8
N1—C5—C18110.73 (15)C13—C14—H14120.4
C6—C5—C18115.47 (19)C15—C14—H14120.4
C5—C6—C7110.75 (19)C10—C15—H15119.2
C5—C6—C19112.7 (2)C14—C15—H15119.2
C7—C6—C19112.5 (2)O2—C16—H161110.0
C6—C7—C8111.5 (2)O2—C16—H162110.0
C7—C8—C9113.4 (2)C17—C16—H161110.0
N1—C9—C8109.7 (2)C17—C16—H162110.0
C1—C10—C11122.00 (17)H161—C16—H162109.5
C1—C10—C15119.68 (15)C16—C17—H171109.5
C11—C10—C15118.3 (2)C16—C17—H172109.5
C10—C11—C12120.77 (18)C16—C17—H173109.5
C11—C12—C13120.40 (18)H171—C17—H172109.5
O2—C13—C12116.04 (18)H171—C17—H173109.5
O2—C13—C14124.1 (2)H172—C17—H173109.5
C12—C13—C14119.8 (2)C5—C18—H181109.5
C13—C14—C15119.2 (2)C5—C18—H182109.5
C10—C15—C14121.56 (16)C5—C18—H183109.5
O2—C16—C17107.6 (2)H181—C18—H182109.5
C1—C2—H21120.0H181—C18—H183109.5
C1—C2—H22120.0H182—C18—H183109.5
C3—C2—H21120.0C6—C19—H191109.5
C3—C2—H22120.0C6—C19—H192109.5
H21—C2—H22109.5C6—C19—H193109.5
N1—C5—H5107.3H191—C19—H192109.5
C6—C5—H5107.3H191—C19—H193109.5
C18—C5—H5107.3H192—C19—H193109.5
C5—C6—H6106.8
C13—O2—C16—C17171.5 (2)C10—C1—C3—Cl10.50 (18)
C16—O2—C13—C12168.6 (2)C10—C1—C3—Cl2143.32 (14)
C16—O2—C13—C1411.4 (3)C10—C1—C3—C2109.02 (17)
C4—N1—C5—C6128.6 (2)C4—C1—C10—C11115.16 (19)
C4—N1—C5—C18103.8 (2)C4—C1—C10—C1561.9 (2)
C5—N1—C4—O1170.1 (2)C10—C1—C4—O184.8 (2)
C5—N1—C4—C16.9 (3)C10—C1—C4—N192.3 (2)
C4—N1—C9—C8130.1 (2)C1—C2—C3—Cl1108.87 (18)
C9—N1—C4—O12.1 (3)C1—C2—C3—Cl2111.92 (17)
C9—N1—C4—C1179.1 (2)N1—C5—C6—C755.3 (2)
C5—N1—C9—C856.9 (2)N1—C5—C6—C19177.69 (19)
C9—N1—C5—C659.0 (2)C18—C5—C6—C769.5 (2)
C9—N1—C5—C1868.6 (2)C18—C5—C6—C1957.5 (2)
C2—C1—C3—Cl1108.52 (16)C5—C6—C7—C853.3 (3)
C2—C1—C3—Cl2107.7 (2)C19—C6—C7—C8179.6 (2)
C2—C1—C4—O1125.0 (2)C6—C7—C8—C951.9 (3)
C2—C1—C4—N157.9 (2)C7—C8—C9—N152.0 (3)
C4—C1—C2—C3104.55 (19)C1—C10—C11—C12175.6 (2)
C2—C1—C10—C1135.5 (2)C1—C10—C15—C14176.4 (2)
C2—C1—C10—C15147.49 (18)C11—C10—C15—C140.8 (3)
C10—C1—C2—C3107.6 (2)C15—C10—C11—C121.4 (3)
C3—C1—C4—O157.2 (2)C10—C11—C12—C130.5 (3)
C3—C1—C4—N1125.7 (2)C11—C12—C13—O2178.8 (2)
C4—C1—C3—Cl1139.81 (15)C11—C12—C13—C141.2 (3)
C4—C1—C3—Cl24.0 (2)O2—C13—C14—C15178.2 (2)
C4—C1—C3—C2111.7 (2)C12—C13—C14—C151.8 (3)
C3—C1—C10—C11103.6 (2)C13—C14—C15—C100.8 (3)
C3—C1—C10—C1579.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.932.403.322 (3)170
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds