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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
CCDC reference: 619034
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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
C19H25Cl2NO2 | F(000) = 784.0 |
Mr = 370.32 | Dx = 1.258 Mg m−3 |
Monoclinic, Cc | Melting point: 432-434 K K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71075 Å |
a = 11.662 (5) Å | Cell parameters from 8522 reflections |
b = 16.242 (8) Å | θ = 3.2–27.5° |
c = 11.398 (5) Å | µ = 0.34 mm−1 |
β = 115.078 (19)° | T = 298 K |
V = 1955.3 (15) Å3 | Chunk, colorless |
Z = 4 | 0.33 × 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-1 | Rint = 0.024 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→15 |
Tmin = 0.888, Tmax = 0.934 | k = −21→21 |
9469 measured reflections | l = −14→14 |
4133 independent reflections | |
Refinement top
Refinement on F2 | (Δ/σ)max < 0.001 |
R[F2 > 2σ(F2)] = 0.034 | Δρmax = 0.32 e Å−3 |
wR(F2) = 0.085 | Δρmin = −0.37 e Å−3 |
S = 1.02 | Extinction correction: Larson (1970), equation 22 |
4133 reflections | Extinction coefficient: 145 (16) |
219 parameters | Absolute structure: Flack (1983), 1889 Friedel Pairs |
H-atom parameters constrained | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.16170 (6) | 0.41375 (4) | 0.32210 (8) | 0.0761 (2) | |
Cl2 | 0.16421 (6) | 0.41874 (4) | 0.06979 (6) | 0.0758 (2) | |
O1 | 0.08258 (12) | 0.23702 (11) | 0.01319 (16) | 0.0682 (4) | |
O2 | 0.10888 (16) | 0.08052 (12) | 0.56676 (18) | 0.0812 (5) | |
N1 | 0.27535 (13) | 0.17874 (11) | 0.07917 (16) | 0.0496 (4) | |
C1 | 0.23125 (14) | 0.27401 (11) | 0.22310 (18) | 0.0417 (4) | |
C2 | 0.34566 (17) | 0.33123 (11) | 0.2730 (2) | 0.0454 (5) | |
C3 | 0.21612 (17) | 0.36614 (12) | 0.2171 (2) | 0.0493 (5) | |
C4 | 0.19111 (16) | 0.22899 (12) | 0.0953 (2) | 0.0471 (5) | |
C5 | 0.40104 (17) | 0.15575 (12) | 0.1801 (2) | 0.0478 (5) | |
C6 | 0.5000 (2) | 0.17168 (13) | 0.1271 (2) | 0.0605 (6) | |
C7 | 0.4654 (2) | 0.1262 (2) | −0.0004 (2) | 0.0838 (9) | |
C8 | 0.3332 (2) | 0.1458 (2) | −0.0964 (2) | 0.0871 (9) | |
C9 | 0.2363 (2) | 0.13407 (17) | −0.0436 (2) | 0.0700 (7) | |
C10 | 0.19811 (16) | 0.22639 (11) | 0.31800 (18) | 0.0410 (4) | |
C11 | 0.28973 (17) | 0.19576 (13) | 0.4321 (2) | 0.0520 (5) | |
C12 | 0.25725 (19) | 0.14796 (16) | 0.5127 (2) | 0.0619 (6) | |
C13 | 0.1316 (2) | 0.13020 (12) | 0.4811 (2) | 0.0565 (6) | |
C14 | 0.03855 (18) | 0.16178 (13) | 0.3695 (2) | 0.0567 (6) | |
C15 | 0.07271 (17) | 0.20922 (12) | 0.2885 (2) | 0.0505 (5) | |
C16 | −0.0141 (2) | 0.04778 (17) | 0.5293 (2) | 0.0796 (9) | |
C17 | −0.0076 (3) | −0.0121 (2) | 0.6285 (3) | 0.1073 (12) | |
C18 | 0.3989 (2) | 0.06890 (13) | 0.2284 (2) | 0.0656 (7) | |
C19 | 0.6334 (2) | 0.15331 (18) | 0.2252 (3) | 0.0821 (8) | |
H5 | 0.4199 | 0.1931 | 0.2535 | 0.057* | |
H6 | 0.4966 | 0.2306 | 0.1077 | 0.073* | |
H11 | 0.3745 | 0.2076 | 0.4547 | 0.062* | |
H12 | 0.3201 | 0.1274 | 0.5890 | 0.074* | |
H14 | −0.0463 | 0.1514 | 0.3487 | 0.068* | |
H15 | 0.0098 | 0.2300 | 0.2124 | 0.061* | |
H21 | 0.3982 | 0.3360 | 0.2263 | 0.055* | |
H22 | 0.3983 | 0.3355 | 0.3653 | 0.055* | |
H71 | 0.4721 | 0.0674 | 0.0161 | 0.101* | |
H72 | 0.5239 | 0.1421 | −0.0365 | 0.101* | |
H81 | 0.3117 | 0.1102 | −0.1710 | 0.105* | |
H82 | 0.3307 | 0.2028 | −0.1229 | 0.105* | |
H91 | 0.2286 | 0.0759 | −0.0291 | 0.084* | |
H92 | 0.1552 | 0.1550 | −0.1054 | 0.084* | |
H161 | −0.0419 | 0.0207 | 0.4459 | 0.095* | |
H162 | −0.0728 | 0.0915 | 0.5236 | 0.095* | |
H171 | −0.0913 | −0.0312 | 0.6104 | 0.129* | |
H172 | 0.0286 | 0.0138 | 0.7121 | 0.129* | |
H173 | 0.0442 | −0.0578 | 0.6278 | 0.129* | |
H181 | 0.3320 | 0.0642 | 0.2560 | 0.079* | |
H182 | 0.4785 | 0.0572 | 0.3000 | 0.079* | |
H183 | 0.3849 | 0.0304 | 0.1597 | 0.079* | |
H191 | 0.6525 | 0.1856 | 0.3017 | 0.098* | |
H192 | 0.6406 | 0.0959 | 0.2471 | 0.098* | |
H193 | 0.6919 | 0.1667 | 0.1890 | 0.098* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0991 (4) | 0.0538 (3) | 0.0995 (5) | 0.0197 (2) | 0.0654 (4) | 0.0008 (3) |
Cl2 | 0.0770 (3) | 0.0750 (4) | 0.0733 (4) | 0.0235 (3) | 0.0299 (3) | 0.0331 (3) |
O1 | 0.0336 (6) | 0.0980 (12) | 0.0572 (9) | 0.0115 (7) | 0.0038 (6) | −0.0132 (8) |
O2 | 0.0746 (11) | 0.0917 (12) | 0.0785 (11) | −0.0144 (9) | 0.0336 (9) | 0.0262 (9) |
N1 | 0.0416 (8) | 0.0587 (10) | 0.0420 (9) | 0.0091 (7) | 0.0114 (7) | −0.0051 (7) |
C1 | 0.0315 (7) | 0.0429 (9) | 0.0500 (10) | 0.0072 (6) | 0.0166 (7) | 0.0035 (8) |
C2 | 0.0392 (9) | 0.0411 (10) | 0.0529 (11) | 0.0033 (7) | 0.0166 (8) | 0.0022 (8) |
C3 | 0.0485 (10) | 0.0454 (10) | 0.0569 (11) | 0.0142 (8) | 0.0252 (9) | 0.0106 (9) |
C4 | 0.0363 (9) | 0.0505 (11) | 0.0522 (12) | 0.0040 (7) | 0.0165 (9) | −0.0002 (8) |
C5 | 0.0380 (8) | 0.0455 (10) | 0.0541 (11) | 0.0090 (7) | 0.0138 (8) | −0.0018 (8) |
C6 | 0.0529 (11) | 0.0543 (12) | 0.0824 (16) | 0.0099 (9) | 0.0365 (11) | 0.0016 (10) |
C7 | 0.0851 (17) | 0.100 (2) | 0.0843 (18) | 0.0258 (15) | 0.0532 (15) | 0.0009 (15) |
C8 | 0.1031 (19) | 0.107 (2) | 0.0574 (15) | 0.0320 (17) | 0.0403 (15) | −0.0032 (14) |
C9 | 0.0661 (14) | 0.0830 (18) | 0.0496 (13) | 0.0167 (12) | 0.0135 (11) | −0.0164 (11) |
C10 | 0.0368 (8) | 0.0388 (9) | 0.0461 (10) | 0.0003 (7) | 0.0163 (8) | −0.0015 (7) |
C11 | 0.0371 (9) | 0.0607 (12) | 0.0525 (12) | −0.0038 (8) | 0.0136 (8) | 0.0067 (9) |
C12 | 0.0519 (11) | 0.0745 (15) | 0.0508 (13) | −0.0036 (10) | 0.0136 (10) | 0.0125 (10) |
C13 | 0.0596 (12) | 0.0534 (12) | 0.0607 (13) | −0.0061 (10) | 0.0295 (10) | 0.0044 (10) |
C14 | 0.0427 (10) | 0.0612 (13) | 0.0701 (15) | −0.0024 (9) | 0.0276 (10) | 0.0034 (10) |
C15 | 0.0393 (9) | 0.0558 (12) | 0.0519 (11) | 0.0086 (8) | 0.0148 (8) | 0.0076 (9) |
C16 | 0.0731 (15) | 0.0769 (17) | 0.103 (2) | −0.0048 (13) | 0.0512 (15) | 0.0194 (16) |
C17 | 0.103 (2) | 0.098 (2) | 0.141 (2) | −0.0088 (17) | 0.070 (2) | 0.034 (2) |
C18 | 0.0659 (13) | 0.0529 (13) | 0.0722 (15) | 0.0062 (10) | 0.0237 (11) | 0.0040 (10) |
C19 | 0.0538 (12) | 0.0837 (18) | 0.112 (2) | 0.0081 (12) | 0.0384 (13) | −0.0035 (16) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.754 (2) | C2—H21 | 0.970 |
Cl2—C3 | 1.748 (2) | C2—H22 | 0.970 |
O1—C4 | 1.2208 (19) | C5—H5 | 0.980 |
O2—C13 | 1.377 (3) | C6—H6 | 0.980 |
O2—C16 | 1.415 (3) | C7—H71 | 0.970 |
N1—C4 | 1.348 (2) | C7—H72 | 0.970 |
N1—C5 | 1.477 (2) | C8—H81 | 0.970 |
N1—C9 | 1.467 (3) | C8—H82 | 0.970 |
C1—C2 | 1.524 (2) | C9—H91 | 0.970 |
C1—C3 | 1.505 (2) | C9—H92 | 0.970 |
C1—C4 | 1.516 (2) | C11—H11 | 0.930 |
C1—C10 | 1.507 (3) | C12—H12 | 0.930 |
C2—C3 | 1.481 (2) | C14—H14 | 0.930 |
C5—C6 | 1.534 (3) | C15—H15 | 0.930 |
C5—C18 | 1.518 (3) | C16—H161 | 0.970 |
C6—C7 | 1.525 (4) | C16—H162 | 0.970 |
C6—C19 | 1.512 (2) | C17—H171 | 0.960 |
C7—C8 | 1.498 (3) | C17—H172 | 0.960 |
C8—C9 | 1.501 (4) | C17—H173 | 0.960 |
C10—C11 | 1.379 (2) | C18—H181 | 0.960 |
C10—C15 | 1.383 (2) | C18—H182 | 0.960 |
C11—C12 | 1.373 (3) | C18—H183 | 0.960 |
C12—C13 | 1.383 (3) | C19—H191 | 0.960 |
C13—C14 | 1.374 (2) | C19—H192 | 0.960 |
C14—C15 | 1.385 (3) | C19—H193 | 0.960 |
C16—C17 | 1.468 (5) | | |
| | | |
C13—O2—C16 | 118.79 (18) | C7—C6—H6 | 106.8 |
C4—N1—C5 | 125.94 (17) | C19—C6—H6 | 106.8 |
C4—N1—C9 | 118.67 (15) | C6—C7—H71 | 109.0 |
C5—N1—C9 | 114.97 (18) | C6—C7—H72 | 109.0 |
C2—C1—C3 | 58.53 (11) | C8—C7—H71 | 109.0 |
C2—C1—C4 | 121.16 (19) | C8—C7—H72 | 109.0 |
C2—C1—C10 | 119.68 (15) | H71—C7—H72 | 109.5 |
C3—C1—C4 | 116.97 (16) | C7—C8—H81 | 108.5 |
C3—C1—C10 | 118.82 (18) | C7—C8—H82 | 108.5 |
C4—C1—C10 | 111.93 (15) | C9—C8—H81 | 108.5 |
C1—C2—C3 | 60.07 (12) | C9—C8—H82 | 108.5 |
Cl1—C3—Cl2 | 111.21 (10) | H81—C8—H82 | 109.5 |
Cl1—C3—C1 | 118.48 (17) | N1—C9—H91 | 109.4 |
Cl1—C3—C2 | 118.26 (14) | N1—C9—H92 | 109.4 |
Cl2—C3—C1 | 121.06 (15) | C8—C9—H91 | 109.4 |
Cl2—C3—C2 | 118.37 (18) | C8—C9—H92 | 109.4 |
C1—C3—C2 | 61.39 (11) | H91—C9—H92 | 109.5 |
O1—C4—N1 | 122.60 (19) | C10—C11—H11 | 119.6 |
O1—C4—C1 | 118.85 (19) | C12—C11—H11 | 119.6 |
N1—C4—C1 | 118.48 (13) | C11—C12—H12 | 119.8 |
N1—C5—C6 | 108.33 (17) | C13—C12—H12 | 119.8 |
N1—C5—C18 | 110.73 (15) | C13—C14—H14 | 120.4 |
C6—C5—C18 | 115.47 (19) | C15—C14—H14 | 120.4 |
C5—C6—C7 | 110.75 (19) | C10—C15—H15 | 119.2 |
C5—C6—C19 | 112.7 (2) | C14—C15—H15 | 119.2 |
C7—C6—C19 | 112.5 (2) | O2—C16—H161 | 110.0 |
C6—C7—C8 | 111.5 (2) | O2—C16—H162 | 110.0 |
C7—C8—C9 | 113.4 (2) | C17—C16—H161 | 110.0 |
N1—C9—C8 | 109.7 (2) | C17—C16—H162 | 110.0 |
C1—C10—C11 | 122.00 (17) | H161—C16—H162 | 109.5 |
C1—C10—C15 | 119.68 (15) | C16—C17—H171 | 109.5 |
C11—C10—C15 | 118.3 (2) | C16—C17—H172 | 109.5 |
C10—C11—C12 | 120.77 (18) | C16—C17—H173 | 109.5 |
C11—C12—C13 | 120.40 (18) | H171—C17—H172 | 109.5 |
O2—C13—C12 | 116.04 (18) | H171—C17—H173 | 109.5 |
O2—C13—C14 | 124.1 (2) | H172—C17—H173 | 109.5 |
C12—C13—C14 | 119.8 (2) | C5—C18—H181 | 109.5 |
C13—C14—C15 | 119.2 (2) | C5—C18—H182 | 109.5 |
C10—C15—C14 | 121.56 (16) | C5—C18—H183 | 109.5 |
O2—C16—C17 | 107.6 (2) | H181—C18—H182 | 109.5 |
C1—C2—H21 | 120.0 | H181—C18—H183 | 109.5 |
C1—C2—H22 | 120.0 | H182—C18—H183 | 109.5 |
C3—C2—H21 | 120.0 | C6—C19—H191 | 109.5 |
C3—C2—H22 | 120.0 | C6—C19—H192 | 109.5 |
H21—C2—H22 | 109.5 | C6—C19—H193 | 109.5 |
N1—C5—H5 | 107.3 | H191—C19—H192 | 109.5 |
C6—C5—H5 | 107.3 | H191—C19—H193 | 109.5 |
C18—C5—H5 | 107.3 | H192—C19—H193 | 109.5 |
C5—C6—H6 | 106.8 | | |
| | | |
C13—O2—C16—C17 | 171.5 (2) | C10—C1—C3—Cl1 | 0.50 (18) |
C16—O2—C13—C12 | −168.6 (2) | C10—C1—C3—Cl2 | −143.32 (14) |
C16—O2—C13—C14 | 11.4 (3) | C10—C1—C3—C2 | 109.02 (17) |
C4—N1—C5—C6 | −128.6 (2) | C4—C1—C10—C11 | 115.16 (19) |
C4—N1—C5—C18 | 103.8 (2) | C4—C1—C10—C15 | −61.9 (2) |
C5—N1—C4—O1 | −170.1 (2) | C10—C1—C4—O1 | 84.8 (2) |
C5—N1—C4—C1 | 6.9 (3) | C10—C1—C4—N1 | −92.3 (2) |
C4—N1—C9—C8 | 130.1 (2) | C1—C2—C3—Cl1 | 108.87 (18) |
C9—N1—C4—O1 | 2.1 (3) | C1—C2—C3—Cl2 | −111.92 (17) |
C9—N1—C4—C1 | 179.1 (2) | N1—C5—C6—C7 | −55.3 (2) |
C5—N1—C9—C8 | −56.9 (2) | N1—C5—C6—C19 | 177.69 (19) |
C9—N1—C5—C6 | 59.0 (2) | C18—C5—C6—C7 | 69.5 (2) |
C9—N1—C5—C18 | −68.6 (2) | C18—C5—C6—C19 | −57.5 (2) |
C2—C1—C3—Cl1 | −108.52 (16) | C5—C6—C7—C8 | 53.3 (3) |
C2—C1—C3—Cl2 | 107.7 (2) | C19—C6—C7—C8 | −179.6 (2) |
C2—C1—C4—O1 | −125.0 (2) | C6—C7—C8—C9 | −51.9 (3) |
C2—C1—C4—N1 | 57.9 (2) | C7—C8—C9—N1 | 52.0 (3) |
C4—C1—C2—C3 | 104.55 (19) | C1—C10—C11—C12 | −175.6 (2) |
C2—C1—C10—C11 | −35.5 (2) | C1—C10—C15—C14 | 176.4 (2) |
C2—C1—C10—C15 | 147.49 (18) | C11—C10—C15—C14 | −0.8 (3) |
C10—C1—C2—C3 | −107.6 (2) | C15—C10—C11—C12 | 1.4 (3) |
C3—C1—C4—O1 | −57.2 (2) | C10—C11—C12—C13 | −0.5 (3) |
C3—C1—C4—N1 | 125.7 (2) | C11—C12—C13—O2 | 178.8 (2) |
C4—C1—C3—Cl1 | 139.81 (15) | C11—C12—C13—C14 | −1.2 (3) |
C4—C1—C3—Cl2 | −4.0 (2) | O2—C13—C14—C15 | −178.2 (2) |
C4—C1—C3—C2 | −111.7 (2) | C12—C13—C14—C15 | 1.8 (3) |
C3—C1—C10—C11 | −103.6 (2) | C13—C14—C15—C10 | −0.8 (3) |
C3—C1—C10—C15 | 79.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.93 | 2.40 | 3.322 (3) | 170 |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |
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