Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060059/rk2063sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060059/rk2063Isup2.hkl |
CCDC reference: 673048
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.124
- Data-to-parameter ratio = 26.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C14 - C15 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C14 - C17 ... 1.44 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2 ..... S PLAT793_ALERT_1_G Check the Absolute Configuration of C6 ..... R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For applications of piperidines, see: Jayabharathi et al. (2007); Manimekalai et al. 2000. For a related crystal structure, see: Thiruvalluvar et al. (2007).
2,6-bis(O-chlorophenyl)piperidin-4-one (3 mmol, 1 g), ammonium acetate (3 mmol, 0.256 g) and basic alumina (3 mmol, 3 g) and malononitrile (3 mmol, 0.02 g) were mixed thoroughly in a mortar. The reaction mixture was placed in a beaker and irradiated using microwave in a microwave oven operating at 2450 Hz (100% power, 850 W) for 3 minutes. The reaction mixture was extracted with dichloromethane followed by water. The product was recrystallized from ethanol. The yield of the isolated product was 0.42 g (60%).
The N bound H atom was obtained from a difference Fourier map and refined isotropically. Other H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.95–1.00 Å and Uiso = 1.2Ueq(C).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C20H15Cl2N3 | F(000) = 760 |
Mr = 368.25 | Dx = 1.356 Mg m−3 |
Monoclinic, P21/c | Melting point: 452 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.1732 (10) Å | Cell parameters from 3546 reflections |
b = 7.5493 (5) Å | θ = 4.7–32.8° |
c = 16.3452 (12) Å | µ = 0.37 mm−1 |
β = 105.494 (7)° | T = 200 K |
V = 1804.3 (2) Å3 | Plate, pale yellow |
Z = 4 | 0.51 × 0.44 × 0.21 mm |
Oxford Diffraction Gemini diffractometer | 6044 independent reflections |
Radiation source: fine–focus sealed tube | 2122 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.8°, θmin = 4.7° |
ϕ and ω scans | h = −22→21 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −11→11 |
Tmin = 0.829, Tmax = 0.926 | l = −17→24 |
17148 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0517P)2] where P = (Fo2 + 2Fc2)/3 |
6044 reflections | (Δ/σ)max < 0.002 |
230 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C20H15Cl2N3 | V = 1804.3 (2) Å3 |
Mr = 368.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.1732 (10) Å | µ = 0.37 mm−1 |
b = 7.5493 (5) Å | T = 200 K |
c = 16.3452 (12) Å | 0.51 × 0.44 × 0.21 mm |
β = 105.494 (7)° |
Oxford Diffraction Gemini diffractometer | 6044 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 2122 reflections with I > 2σ(I) |
Tmin = 0.829, Tmax = 0.926 | Rint = 0.050 |
17148 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | Δρmax = 0.22 e Å−3 |
6044 reflections | Δρmin = −0.32 e Å−3 |
230 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All s.u.'s are estimated from the variances of the (full) variance–covariance matrix. The cell s.u.'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 > 2σ(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 | ||
Cl1 | 0.51594 (3) | 0.83403 (7) | 0.09858 (4) | 0.0614 (2) | |
Cl2 | 0.20649 (5) | 0.40648 (8) | 0.32315 (5) | 0.0862 (3) | |
N1 | 0.27010 (10) | 0.8856 (2) | 0.19991 (11) | 0.0415 (5) | |
N16 | 0.32725 (12) | 0.4937 (3) | −0.09216 (11) | 0.0692 (7) | |
N18 | 0.12217 (15) | 0.2456 (3) | 0.01170 (14) | 0.0857 (9) | |
C2 | 0.33512 (11) | 0.8643 (2) | 0.14911 (11) | 0.0391 (6) | |
C3 | 0.28114 (13) | 0.8191 (2) | 0.05805 (12) | 0.0459 (6) | |
C4 | 0.22329 (11) | 0.6593 (3) | 0.05782 (12) | 0.0432 (6) | |
C5 | 0.16425 (12) | 0.6703 (3) | 0.11789 (12) | 0.0517 (7) | |
C6 | 0.22218 (11) | 0.7209 (2) | 0.20674 (11) | 0.0416 (6) | |
C14 | 0.22543 (11) | 0.5155 (3) | 0.01047 (11) | 0.0434 (6) | |
C15 | 0.28311 (13) | 0.5028 (3) | −0.04622 (12) | 0.0486 (7) | |
C17 | 0.16823 (14) | 0.3631 (3) | 0.01110 (13) | 0.0554 (8) | |
C21 | 0.39066 (11) | 1.0311 (2) | 0.15015 (10) | 0.0374 (6) | |
C22 | 0.47250 (12) | 1.0308 (3) | 0.12742 (11) | 0.0429 (6) | |
C23 | 0.52285 (13) | 1.1825 (3) | 0.12783 (12) | 0.0508 (7) | |
C24 | 0.49203 (13) | 1.3408 (3) | 0.15060 (13) | 0.0547 (7) | |
C25 | 0.41203 (14) | 1.3466 (3) | 0.17392 (14) | 0.0559 (7) | |
C26 | 0.36109 (12) | 1.1931 (2) | 0.17297 (12) | 0.0476 (7) | |
C61 | 0.16153 (11) | 0.7413 (3) | 0.26566 (11) | 0.0414 (6) | |
C62 | 0.14843 (12) | 0.6070 (3) | 0.31873 (12) | 0.0472 (7) | |
C63 | 0.08924 (13) | 0.6248 (3) | 0.36937 (12) | 0.0599 (8) | |
C64 | 0.04183 (13) | 0.7797 (4) | 0.36721 (13) | 0.0651 (9) | |
C65 | 0.05376 (13) | 0.9164 (3) | 0.31606 (14) | 0.0636 (8) | |
C66 | 0.11242 (12) | 0.8965 (3) | 0.26533 (13) | 0.0535 (7) | |
H1 | 0.2970 (12) | 0.917 (3) | 0.2470 (12) | 0.049 (6)* | |
H2 | 0.37742 | 0.76416 | 0.17265 | 0.0469* | |
H3A | 0.24184 | 0.92063 | 0.03298 | 0.0550* | |
H3B | 0.32408 | 0.79641 | 0.02306 | 0.0550* | |
H5A | 0.13441 | 0.55450 | 0.12023 | 0.0620* | |
H5B | 0.11581 | 0.76006 | 0.09739 | 0.0620* | |
H6 | 0.26803 | 0.62538 | 0.22874 | 0.0499* | |
H23 | 0.57886 | 1.17760 | 0.11236 | 0.0610* | |
H24 | 0.52616 | 1.44608 | 0.15019 | 0.0656* | |
H25 | 0.39118 | 1.45574 | 0.19082 | 0.0671* | |
H26 | 0.30499 | 1.19933 | 0.18823 | 0.0571* | |
H63 | 0.08152 | 0.53052 | 0.40532 | 0.0719* | |
H64 | 0.00043 | 0.79258 | 0.40135 | 0.0781* | |
H65 | 0.02166 | 1.02463 | 0.31559 | 0.0763* | |
H66 | 0.11943 | 0.99116 | 0.22929 | 0.0642* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0679 (3) | 0.0520 (3) | 0.0765 (4) | 0.0007 (2) | 0.0403 (3) | −0.0093 (3) |
Cl2 | 0.1155 (5) | 0.0572 (4) | 0.1071 (5) | 0.0202 (3) | 0.0665 (4) | 0.0268 (4) |
N1 | 0.0461 (9) | 0.0446 (10) | 0.0375 (9) | −0.0067 (7) | 0.0176 (8) | −0.0067 (9) |
N16 | 0.0757 (12) | 0.0742 (14) | 0.0707 (12) | −0.0104 (10) | 0.0422 (10) | −0.0109 (11) |
N18 | 0.1039 (15) | 0.0733 (14) | 0.1018 (16) | −0.0402 (12) | 0.0655 (13) | −0.0354 (13) |
C2 | 0.0453 (10) | 0.0367 (10) | 0.0371 (10) | −0.0036 (8) | 0.0143 (8) | −0.0019 (9) |
C3 | 0.0547 (10) | 0.0442 (11) | 0.0428 (11) | −0.0087 (9) | 0.0202 (9) | −0.0059 (10) |
C4 | 0.0426 (10) | 0.0504 (12) | 0.0376 (10) | −0.0071 (8) | 0.0123 (8) | −0.0057 (10) |
C5 | 0.0494 (10) | 0.0574 (13) | 0.0557 (12) | −0.0130 (9) | 0.0269 (10) | −0.0140 (11) |
C6 | 0.0415 (9) | 0.0411 (10) | 0.0468 (11) | −0.0012 (8) | 0.0197 (8) | −0.0005 (10) |
C14 | 0.0467 (10) | 0.0477 (12) | 0.0376 (10) | −0.0066 (8) | 0.0146 (8) | −0.0035 (10) |
C15 | 0.0532 (11) | 0.0473 (12) | 0.0478 (11) | −0.0081 (9) | 0.0179 (9) | −0.0096 (11) |
C17 | 0.0639 (12) | 0.0575 (14) | 0.0542 (13) | −0.0150 (10) | 0.0319 (10) | −0.0207 (12) |
C21 | 0.0460 (10) | 0.0353 (10) | 0.0319 (9) | −0.0002 (8) | 0.0123 (8) | 0.0017 (9) |
C22 | 0.0518 (10) | 0.0400 (11) | 0.0399 (10) | −0.0045 (8) | 0.0176 (9) | −0.0044 (10) |
C23 | 0.0515 (11) | 0.0539 (13) | 0.0493 (12) | −0.0107 (10) | 0.0173 (9) | 0.0012 (11) |
C24 | 0.0613 (12) | 0.0424 (12) | 0.0571 (13) | −0.0134 (10) | 0.0101 (10) | 0.0045 (11) |
C25 | 0.0664 (13) | 0.0360 (11) | 0.0638 (14) | −0.0008 (10) | 0.0148 (10) | −0.0037 (11) |
C26 | 0.0491 (10) | 0.0413 (11) | 0.0537 (13) | 0.0024 (8) | 0.0160 (9) | 0.0010 (10) |
C61 | 0.0369 (9) | 0.0475 (11) | 0.0411 (11) | −0.0007 (8) | 0.0126 (8) | −0.0017 (10) |
C62 | 0.0478 (10) | 0.0481 (12) | 0.0492 (12) | −0.0017 (9) | 0.0191 (9) | 0.0014 (11) |
C63 | 0.0563 (12) | 0.0814 (16) | 0.0459 (12) | −0.0101 (11) | 0.0202 (10) | 0.0072 (13) |
C64 | 0.0463 (12) | 0.105 (2) | 0.0506 (13) | 0.0043 (12) | 0.0242 (10) | −0.0030 (15) |
C65 | 0.0535 (12) | 0.0791 (17) | 0.0619 (14) | 0.0208 (11) | 0.0220 (10) | −0.0030 (14) |
C66 | 0.0526 (11) | 0.0568 (13) | 0.0553 (12) | 0.0118 (10) | 0.0215 (10) | 0.0070 (12) |
Cl1—C22 | 1.741 (2) | C25—C26 | 1.391 (3) |
Cl2—C62 | 1.743 (2) | C61—C66 | 1.388 (3) |
N1—C2 | 1.458 (2) | C61—C62 | 1.383 (3) |
N1—C6 | 1.460 (2) | C62—C63 | 1.381 (3) |
N16—C15 | 1.134 (3) | C63—C64 | 1.368 (4) |
N18—C17 | 1.131 (3) | C64—C65 | 1.370 (3) |
N1—H1 | 0.81 (2) | C65—C66 | 1.377 (3) |
C2—C21 | 1.513 (2) | C2—H2 | 1.0000 |
C2—C3 | 1.533 (3) | C3—H3A | 0.9900 |
C3—C4 | 1.491 (3) | C3—H3B | 0.9900 |
C4—C14 | 1.339 (3) | C5—H5A | 0.9900 |
C4—C5 | 1.498 (3) | C5—H5B | 0.9900 |
C5—C6 | 1.532 (3) | C6—H6 | 1.0000 |
C6—C61 | 1.507 (2) | C23—H23 | 0.9500 |
C14—C17 | 1.443 (3) | C24—H24 | 0.9500 |
C14—C15 | 1.438 (3) | C25—H25 | 0.9500 |
C21—C22 | 1.388 (3) | C26—H26 | 0.9500 |
C21—C26 | 1.388 (2) | C63—H63 | 0.9500 |
C22—C23 | 1.376 (3) | C64—H64 | 0.9500 |
C23—C24 | 1.371 (3) | C65—H65 | 0.9500 |
C24—C25 | 1.367 (3) | C66—H66 | 0.9500 |
Cl1···C3 | 3.447 (2) | C65···C63xi | 3.586 (3) |
Cl1···C25i | 3.586 (2) | C66···C15x | 3.537 (3) |
Cl1···N16ii | 3.454 (2) | C15···H3B | 2.4900 |
Cl1···C23iii | 3.591 (2) | C17···H5A | 2.4500 |
Cl1···H2 | 2.7400 | C22···H3B | 3.0100 |
Cl1···H3B | 2.8600 | C24···H2viii | 3.0900 |
Cl1···H24iv | 3.0400 | C26···H1 | 2.72 (2) |
Cl2···H6 | 2.6000 | C62···H65vi | 2.9700 |
N16···C24iii | 3.375 (3) | C63···H3Ax | 3.0500 |
N16···Cl1ii | 3.454 (2) | C66···H1 | 2.899 (19) |
N1···H66 | 2.5800 | C66···H5B | 2.9500 |
N1···H26 | 2.4500 | H1···C26 | 2.72 (2) |
N16···H23iii | 2.9200 | H1···C66 | 2.899 (19) |
N16···H24iii | 2.6800 | H1···H26 | 2.3500 |
N16···H1v | 2.633 (19) | H1···N16x | 2.633 (19) |
N18···H5A | 2.9100 | H2···Cl1 | 2.7400 |
N18···H64vi | 2.6500 | H2···H6 | 2.3500 |
N18···H63vii | 2.6800 | H2···H25iv | 2.3500 |
C3···Cl1 | 3.447 (2) | H2···C24i | 3.0900 |
C4···C63v | 3.596 (3) | H3A···C63v | 3.0500 |
C4···C64v | 3.594 (3) | H3B···Cl1 | 2.8600 |
C14···C25iv | 3.569 (3) | H3B···C15 | 2.4900 |
C14···C64v | 3.486 (3) | H3B···C22 | 3.0100 |
C14···C65v | 3.567 (3) | H5A···N18 | 2.9100 |
C15···C66v | 3.537 (3) | H5A···C17 | 2.4500 |
C21···C24i | 3.570 (3) | H5B···C66 | 2.9500 |
C22···C25i | 3.537 (3) | H6···Cl2 | 2.6000 |
C23···Cl1iii | 3.591 (2) | H6···H2 | 2.3500 |
C24···N16iii | 3.375 (3) | H6···H25iv | 2.4800 |
C24···C21viii | 3.570 (3) | H23···N16iii | 2.9200 |
C25···Cl1viii | 3.586 (2) | H24···Cl1ix | 3.0400 |
C25···C14ix | 3.569 (3) | H24···N16iii | 2.6800 |
C25···C22viii | 3.537 (3) | H25···H2ix | 2.3500 |
C62···C65vi | 3.567 (3) | H25···H6ix | 2.4800 |
C63···C4x | 3.596 (3) | H26···N1 | 2.4500 |
C63···C65vi | 3.586 (3) | H26···H1 | 2.3500 |
C64···C4x | 3.594 (3) | H63···N18xii | 2.6800 |
C64···C14x | 3.486 (3) | H64···N18xi | 2.6500 |
C65···C14x | 3.567 (3) | H65···C62xi | 2.9700 |
C65···C62xi | 3.567 (3) | H66···N1 | 2.5800 |
C2—N1—C6 | 112.10 (14) | C63—C64—C65 | 120.34 (19) |
C6—N1—H1 | 108.3 (15) | C64—C65—C66 | 119.8 (2) |
C2—N1—H1 | 109.3 (13) | C61—C66—C65 | 121.5 (2) |
N1—C2—C21 | 111.19 (13) | N1—C2—H2 | 109.00 |
N1—C2—C3 | 108.06 (15) | C3—C2—H2 | 109.00 |
C3—C2—C21 | 110.34 (14) | C21—C2—H2 | 109.00 |
C2—C3—C4 | 110.11 (15) | C2—C3—H3A | 110.00 |
C3—C4—C5 | 114.09 (18) | C2—C3—H3B | 110.00 |
C5—C4—C14 | 122.35 (19) | C4—C3—H3A | 110.00 |
C3—C4—C14 | 123.53 (17) | C4—C3—H3B | 110.00 |
C4—C5—C6 | 110.07 (15) | H3A—C3—H3B | 108.00 |
N1—C6—C61 | 111.32 (15) | C4—C5—H5A | 110.00 |
C5—C6—C61 | 109.74 (14) | C4—C5—H5B | 110.00 |
N1—C6—C5 | 108.14 (15) | C6—C5—H5A | 110.00 |
C15—C14—C17 | 114.98 (19) | C6—C5—H5B | 110.00 |
C4—C14—C15 | 122.66 (19) | H5A—C5—H5B | 108.00 |
C4—C14—C17 | 122.34 (17) | N1—C6—H6 | 109.00 |
N16—C15—C14 | 178.7 (2) | C5—C6—H6 | 109.00 |
N18—C17—C14 | 178.8 (2) | C61—C6—H6 | 109.00 |
C2—C21—C26 | 121.17 (15) | C22—C23—H23 | 120.00 |
C2—C21—C22 | 122.08 (16) | C24—C23—H23 | 120.00 |
C22—C21—C26 | 116.75 (16) | C23—C24—H24 | 120.00 |
Cl1—C22—C23 | 117.51 (15) | C25—C24—H24 | 120.00 |
Cl1—C22—C21 | 120.30 (16) | C24—C25—H25 | 120.00 |
C21—C22—C23 | 122.19 (19) | C26—C25—H25 | 120.00 |
C22—C23—C24 | 119.86 (19) | C21—C26—H26 | 119.00 |
C23—C24—C25 | 119.8 (2) | C25—C26—H26 | 119.00 |
C24—C25—C26 | 120.2 (2) | C62—C63—H63 | 120.00 |
C21—C26—C25 | 121.25 (18) | C64—C63—H63 | 120.00 |
C62—C61—C66 | 117.03 (17) | C63—C64—H64 | 120.00 |
C6—C61—C62 | 122.72 (18) | C65—C64—H64 | 120.00 |
C6—C61—C66 | 120.18 (17) | C64—C65—H65 | 120.00 |
C61—C62—C63 | 122.0 (2) | C66—C65—H65 | 120.00 |
Cl2—C62—C61 | 120.46 (15) | C61—C66—H66 | 119.00 |
Cl2—C62—C63 | 117.52 (17) | C65—C66—H66 | 119.00 |
C62—C63—C64 | 119.3 (2) | ||
C6—N1—C2—C3 | 64.46 (17) | C5—C6—C61—C66 | −80.5 (2) |
C6—N1—C2—C21 | −174.30 (14) | C2—C21—C22—Cl1 | −1.4 (2) |
C2—N1—C6—C5 | −64.40 (18) | C2—C21—C22—C23 | 179.60 (16) |
C2—N1—C6—C61 | 174.98 (14) | C26—C21—C22—Cl1 | 179.49 (13) |
N1—C2—C3—C4 | −55.69 (18) | C26—C21—C22—C23 | 0.5 (3) |
C21—C2—C3—C4 | −177.45 (15) | C2—C21—C26—C25 | −179.97 (17) |
N1—C2—C21—C22 | 161.78 (16) | C22—C21—C26—C25 | −0.8 (3) |
N1—C2—C21—C26 | −19.1 (2) | Cl1—C22—C23—C24 | −179.57 (15) |
C3—C2—C21—C22 | −78.3 (2) | C21—C22—C23—C24 | −0.5 (3) |
C3—C2—C21—C26 | 100.77 (19) | C22—C23—C24—C25 | 0.9 (3) |
C2—C3—C4—C5 | 51.7 (2) | C23—C24—C25—C26 | −1.3 (3) |
C2—C3—C4—C14 | −126.22 (19) | C24—C25—C26—C21 | 1.2 (3) |
C3—C4—C5—C6 | −51.6 (2) | C6—C61—C62—Cl2 | 2.7 (3) |
C14—C4—C5—C6 | 126.36 (19) | C6—C61—C62—C63 | −176.83 (18) |
C3—C4—C14—C15 | −1.1 (3) | C66—C61—C62—Cl2 | 179.61 (15) |
C3—C4—C14—C17 | −179.60 (18) | C66—C61—C62—C63 | 0.1 (3) |
C5—C4—C14—C15 | −178.89 (18) | C6—C61—C66—C65 | 177.46 (18) |
C5—C4—C14—C17 | 2.6 (3) | C62—C61—C66—C65 | 0.5 (3) |
C4—C5—C6—N1 | 55.4 (2) | Cl2—C62—C63—C64 | −179.49 (16) |
C4—C5—C6—C61 | 176.97 (17) | C61—C62—C63—C64 | 0.1 (3) |
N1—C6—C61—C62 | −144.01 (18) | C62—C63—C64—C65 | −0.7 (3) |
N1—C6—C61—C66 | 39.2 (2) | C63—C64—C65—C66 | 1.3 (3) |
C5—C6—C61—C62 | 96.3 (2) | C64—C65—C66—C61 | −1.2 (3) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) x, y−1, z; (v) x, −y+3/2, z−1/2; (vi) −x, y−1/2, −z+1/2; (vii) x, −y+1/2, z−1/2; (viii) −x+1, y+1/2, −z+1/2; (ix) x, y+1, z; (x) x, −y+3/2, z+1/2; (xi) −x, y+1/2, −z+1/2; (xii) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cl1 | 1.00 | 2.74 | 3.0777 (18) | 100.00 |
C6—H6···Cl2 | 1.00 | 2.60 | 3.0909 (18) | 110.00 |
C26—H26···N1 | 0.95 | 2.45 | 2.795 (2) | 102.00 |
Experimental details
Crystal data | |
Chemical formula | C20H15Cl2N3 |
Mr | 368.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 15.1732 (10), 7.5493 (5), 16.3452 (12) |
β (°) | 105.494 (7) |
V (Å3) | 1804.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.51 × 0.44 × 0.21 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.829, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17148, 6044, 2122 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.762 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.124, 0.89 |
No. of reflections | 6044 |
No. of parameters | 230 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.32 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cl1 | 1.00 | 2.74 | 3.0777 (18) | 100.00 |
C6—H6···Cl2 | 1.00 | 2.60 | 3.0909 (18) | 110.00 |
C26—H26···N1 | 0.95 | 2.45 | 2.795 (2) | 102.00 |
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Jayabharathi et al. (2007) have reported synthesis, stereochemistry and antimicrobial evaluation of t3-benzyl-r2,c6-diarylpiperidin-4-one and its derivatives. Manimekalai et al. (2000) have reported 13C– and 1H-NMR spectral studies of some t3-carboxyethyl-r2,c6-diphenylpiperidine derivatives. Thiruvalluvar et al. (2007) have reported a crystal structure of 3-ethyl-2,6-diphenylpiperidin-4-ol wherein the piperidine ring is in chair form. The piperidine ring of the title molecule, C20H15Cl2N3, is in chair form too. The dihedral angle between the two chlorophenyl rings is 38.4 (1)°. The phenyl rings at 2 and 6 positions are in equatorial orientations. The malononitrile group at position 4 has a coplanar orientation. Weak C—H···Cl and C—H···N intramolecular hydrogen bonds are found in the crystal structure.