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The revived interest in halogen bonding as a tool in pharmaceutical cocrystals and drug design has indicated that cyano–halogen interactions could play an important role. The crystal structures of four closely related δ-keto esters, which differ only in the substitution at a single C atom (by H, OMe, Cl and Br), are compared, namely ethyl 2-cyano-5-oxo-5-phenyl-3-(piperidin-1-yl)pent-2-en­oate, C19H22N2O3, (1), ethyl 2-cyano-5-(4-methoxyphenyl)-5-oxo-3-(piperi­din-1-yl)pent-2-enoate, C20H24N2O4, (2), ethyl 5-(4-chlorophenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C19H21ClN2O3, (3), and the previously published ethyl 5-(4-bromo­phenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C19H21BrN2O3, (4) [Maurya, Vasudev & Gupta (2013). RSC Adv. 3, 12955–12962]. The molecular conformations are very similar, while there are differences in the molecular assemblies. Intermolecular C—H...O hydrogen bonds are found to be the primary interactions in the crystal packing and are present in all four structures. The halogenated derivatives have additional aromatic–aromatic interactions and cyano–halogen interactions, further stabilizing the molecular packing. A database analysis of cyano–halogen interactions using the Cambridge Structural Database [CSD; Groom & Allen (2014). Angew. Chem. Int. Ed. 53, 662–671] revealed that about 13% of the organic molecular crystals containing both cyano and halogen groups have cyano–halogen interactions in their packing. Three geometric parameters for the C—X...N[triple bond]C interaction (X = F, Cl, Br or I), viz. the N...X distance and the C—X...N and C—N...X angles, were analysed. The results indicate that all the short cyano–halogen contacts in the CSD can be classified as halogen bonds, which are directional noncovalent interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615017106/fn3205sup1.cif
Contains datablocks 1, 2, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615017106/fn32051sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615017106/fn32052sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615017106/fn32053sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615017106/fn32054sup5.hkl
Contains datablock 4

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229615017106/fn3205sup6.pdf
Supplementary material

CCDC references: 1424077; 1424078; 1424079; 1424080

Experimental top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Results and discussion top

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(1) Ethyl 2-cyano-5-oxo-5-phenyl-3-(piperidin-1-yl)pent-2-enoate top
Crystal data top
C19H22N2O3Z = 4
Mr = 326.38F(000) = 696
Monoclinic, P21/nDx = 1.243 Mg m3
a = 12.4152 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9071 (6) ŵ = 0.09 mm1
c = 16.5072 (12) ÅT = 293 K
β = 107.194 (2)°Needle, colourless
V = 1743.8 (2) Å30.60 × 0.06 × 0.02 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.044
Radiation source: fine-focus sealed tubeθmax = 26.4°, θmin = 2.4°
7982 measured reflectionsh = 1510
3550 independent reflectionsk = 1110
2211 reflections with I > 2σ(I)l = 2020
Refinement top
Refinement on F23 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.140 w = 1/[σ2(Fo2) + (0.0716P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.010
3550 reflectionsΔρmax = 0.22 e Å3
217 parametersΔρmin = 0.26 e Å3
Crystal data top
C19H22N2O3V = 1743.8 (2) Å3
Mr = 326.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.4152 (10) ŵ = 0.09 mm1
b = 8.9071 (6) ÅT = 293 K
c = 16.5072 (12) Å0.60 × 0.06 × 0.02 mm
β = 107.194 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2211 reflections with I > 2σ(I)
7982 measured reflectionsRint = 0.044
3550 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0523 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.02Δρmax = 0.22 e Å3
3550 reflectionsΔρmin = 0.26 e Å3
217 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.32648 (11)0.56311 (16)1.00253 (8)0.0284 (4)
O20.33697 (11)0.54287 (16)0.86947 (8)0.0288 (4)
O30.11852 (11)0.48808 (17)0.68463 (8)0.0283 (4)
N10.12498 (14)0.3743 (2)1.04256 (10)0.0282 (4)
N20.03660 (13)0.29112 (18)0.81128 (9)0.0225 (4)
C10.4218 (2)0.7376 (3)1.10630 (14)0.0572 (8)
H1A0.47960.81301.12110.086*
H1B0.35070.78161.10510.086*
H1C0.43970.65841.14760.086*
C20.41450 (18)0.6752 (3)1.02088 (13)0.0345 (6)
H2A0.39630.75400.97840.041*
H2B0.48580.63021.02120.041*
C30.29118 (16)0.5089 (2)0.92260 (12)0.0222 (5)
C40.19338 (16)0.4136 (2)0.91138 (11)0.0196 (4)
C50.14377 (16)0.3357 (2)0.83540 (11)0.0208 (5)
C60.21694 (16)0.2989 (2)0.77979 (11)0.0228 (5)
H6A0.20200.19650.75960.027*
H6B0.29550.30480.81340.027*
C70.19787 (16)0.4025 (2)0.70460 (11)0.0215 (5)
C80.28030 (16)0.3948 (2)0.65449 (11)0.0213 (5)
C90.26664 (17)0.4907 (2)0.58593 (12)0.0263 (5)
H90.20760.55950.57260.032*
C100.33996 (19)0.4847 (3)0.53743 (13)0.0308 (5)
H100.33080.55000.49190.037*
C110.42705 (18)0.3818 (2)0.55653 (13)0.0321 (5)
H110.47600.37730.52350.039*
C120.44167 (18)0.2856 (2)0.62433 (13)0.0296 (5)
H120.50060.21670.63710.036*
C130.36863 (17)0.2916 (2)0.67341 (12)0.0242 (5)
H130.37850.22660.71910.029*
C140.01074 (17)0.1785 (2)0.74437 (12)0.0299 (5)
H14A0.03670.09230.76920.036*
H14B0.04800.14480.72080.036*
C150.10796 (18)0.2415 (3)0.67380 (12)0.0348 (6)
H15A0.08050.32030.64450.042*
H15B0.13990.16280.63320.042*
C160.19830 (17)0.3042 (3)0.70906 (13)0.0340 (6)
H16A0.25620.35280.66410.041*
H16B0.23310.22300.73150.041*
C170.14767 (17)0.4158 (2)0.77833 (12)0.0282 (5)
H17A0.20530.44880.80320.034*
H17B0.12210.50290.75390.034*
C180.04958 (16)0.3512 (2)0.84731 (11)0.0251 (5)
H18A0.01660.42890.88830.030*
H18B0.07640.27160.87660.030*
C190.15396 (15)0.3952 (2)0.98361 (12)0.0210 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0253 (8)0.0295 (9)0.0276 (7)0.0095 (7)0.0036 (6)0.0025 (7)
O20.0266 (8)0.0312 (9)0.0304 (8)0.0010 (7)0.0113 (7)0.0051 (7)
O30.0267 (9)0.0271 (9)0.0317 (7)0.0064 (7)0.0094 (6)0.0051 (7)
N10.0267 (10)0.0335 (11)0.0248 (9)0.0011 (9)0.0084 (8)0.0014 (8)
N20.0216 (9)0.0238 (10)0.0218 (8)0.0009 (8)0.0060 (7)0.0038 (8)
C10.0667 (19)0.0504 (18)0.0425 (14)0.0253 (16)0.0022 (13)0.0074 (14)
C20.0247 (12)0.0276 (13)0.0462 (13)0.0058 (10)0.0028 (10)0.0010 (11)
C30.0198 (10)0.0207 (11)0.0251 (10)0.0042 (9)0.0052 (8)0.0031 (9)
C40.0184 (10)0.0219 (11)0.0191 (9)0.0018 (9)0.0063 (8)0.0032 (9)
C50.0224 (11)0.0197 (11)0.0204 (9)0.0036 (9)0.0065 (8)0.0042 (9)
C60.0226 (11)0.0227 (12)0.0235 (10)0.0034 (9)0.0075 (8)0.0011 (9)
C70.0223 (11)0.0185 (11)0.0231 (10)0.0024 (9)0.0059 (8)0.0035 (9)
C80.0234 (11)0.0194 (11)0.0217 (9)0.0032 (9)0.0075 (8)0.0048 (9)
C90.0306 (12)0.0212 (12)0.0277 (10)0.0021 (10)0.0094 (9)0.0006 (9)
C100.0422 (14)0.0270 (13)0.0265 (11)0.0055 (11)0.0152 (10)0.0014 (10)
C110.0392 (13)0.0282 (13)0.0367 (11)0.0088 (11)0.0231 (10)0.0052 (11)
C120.0296 (12)0.0261 (13)0.0374 (11)0.0008 (10)0.0163 (10)0.0038 (10)
C130.0286 (12)0.0210 (12)0.0242 (10)0.0025 (10)0.0097 (9)0.0000 (9)
C140.0286 (12)0.0283 (13)0.0328 (11)0.0016 (10)0.0090 (9)0.0110 (10)
C150.0327 (12)0.0402 (15)0.0286 (11)0.0066 (11)0.0047 (10)0.0131 (11)
C160.0258 (12)0.0397 (15)0.0312 (11)0.0003 (11)0.0002 (9)0.0067 (11)
C170.0235 (11)0.0289 (13)0.0313 (11)0.0018 (10)0.0066 (9)0.0036 (10)
C180.0228 (11)0.0293 (13)0.0244 (10)0.0004 (10)0.0089 (9)0.0029 (9)
C190.0167 (10)0.0203 (11)0.0241 (10)0.0013 (9)0.0031 (8)0.0021 (9)
Geometric parameters (Å, º) top
O1—C31.351 (2)C9—C101.380 (3)
O1—C21.444 (2)C9—H90.9300
O2—C31.216 (2)C10—C111.381 (3)
O3—C71.212 (2)C10—H100.9300
N1—C191.148 (2)C11—C121.378 (3)
N2—C51.332 (2)C11—H110.9300
N2—C181.470 (2)C12—C131.384 (3)
N2—C141.479 (2)C12—H120.9300
C1—C21.494 (3)C13—H130.9300
C1—H1A0.9600C14—C151.516 (3)
C1—H1B0.9600C14—H14A0.9700
C1—H1C0.9600C14—H14B0.9700
C2—H2A0.9700C15—C161.515 (3)
C2—H2B0.9700C15—H15A0.9700
C3—C41.448 (3)C15—H15B0.9700
C4—C51.406 (3)C16—C171.505 (3)
C4—C191.426 (3)C16—H16A0.9700
C5—C61.506 (2)C16—H16B0.9700
C6—C71.508 (3)C17—C181.514 (3)
C6—H6A0.9700C17—H17A0.9700
C6—H6B0.9700C17—H17B0.9700
C7—C81.495 (3)C18—H18A0.9700
C8—C91.388 (3)C18—H18B0.9700
C8—C131.394 (3)
C3—O1—C2117.30 (15)C9—C10—H10120.0
C5—N2—C18123.58 (16)C12—C11—C10120.3 (2)
C5—N2—C14124.52 (16)C12—C11—H11119.8
C18—N2—C14111.89 (15)C10—C11—H11119.8
C2—C1—H1A109.5C11—C12—C13120.0 (2)
C2—C1—H1B109.5C11—C12—H12120.0
H1A—C1—H1B109.5C13—C12—H12120.0
C2—C1—H1C109.5C12—C13—C8120.17 (18)
H1A—C1—H1C109.5C12—C13—H13119.9
H1B—C1—H1C109.5C8—C13—H13119.9
O1—C2—C1106.63 (18)N2—C14—C15111.93 (17)
O1—C2—H2A110.4N2—C14—H14A109.2
C1—C2—H2A110.4C15—C14—H14A109.2
O1—C2—H2B110.4N2—C14—H14B109.2
C1—C2—H2B110.4C15—C14—H14B109.2
H2A—C2—H2B108.6H14A—C14—H14B107.9
O2—C3—O1122.00 (18)C16—C15—C14110.66 (16)
O2—C3—C4127.36 (18)C16—C15—H15A109.5
O1—C3—C4110.61 (16)C14—C15—H15A109.5
C5—C4—C19121.38 (17)C16—C15—H15B109.5
C5—C4—C3122.22 (17)C14—C15—H15B109.5
C19—C4—C3116.28 (16)H15A—C15—H15B108.1
N2—C5—C4123.31 (17)C17—C16—C15110.18 (17)
N2—C5—C6118.85 (16)C17—C16—H16A109.6
C4—C5—C6117.83 (17)C15—C16—H16A109.6
C5—C6—C7113.11 (16)C17—C16—H16B109.6
C5—C6—H6A109.0C15—C16—H16B109.6
C7—C6—H6A109.0H16A—C16—H16B108.1
C5—C6—H6B109.0C16—C17—C18112.51 (18)
C7—C6—H6B109.0C16—C17—H17A109.1
H6A—C6—H6B107.8C18—C17—H17A109.1
O3—C7—C8120.84 (17)C16—C17—H17B109.1
O3—C7—C6121.74 (17)C18—C17—H17B109.1
C8—C7—C6117.42 (17)H17A—C17—H17B107.8
C9—C8—C13119.14 (18)N2—C18—C17110.73 (15)
C9—C8—C7118.96 (18)N2—C18—H18A109.5
C13—C8—C7121.87 (17)C17—C18—H18A109.5
C10—C9—C8120.5 (2)N2—C18—H18B109.5
C10—C9—H9119.8C17—C18—H18B109.5
C8—C9—H9119.8H18A—C18—H18B108.1
C11—C10—C9119.96 (19)N1—C19—C4176.9 (2)
C11—C10—H10120.0
C3—O1—C2—C1169.00 (18)C6—C7—C8—C9178.69 (17)
C2—O1—C3—O25.9 (3)O3—C7—C8—C13176.41 (18)
C2—O1—C3—C4172.36 (17)C6—C7—C8—C133.0 (3)
O2—C3—C4—C55.7 (3)C13—C8—C9—C100.4 (3)
O1—C3—C4—C5176.15 (18)C7—C8—C9—C10178.84 (18)
O2—C3—C4—C19178.1 (2)C8—C9—C10—C110.6 (3)
O1—C3—C4—C190.0 (2)C9—C10—C11—C120.5 (3)
C18—N2—C5—C417.2 (3)C10—C11—C12—C130.2 (3)
C14—N2—C5—C4164.10 (18)C11—C12—C13—C80.0 (3)
C18—N2—C5—C6163.92 (17)C9—C8—C13—C120.1 (3)
C14—N2—C5—C614.8 (3)C7—C8—C13—C12178.50 (17)
C19—C4—C5—N228.0 (3)C5—N2—C14—C15122.1 (2)
C3—C4—C5—N2156.07 (19)C18—N2—C14—C1556.7 (2)
C19—C4—C5—C6150.89 (18)N2—C14—C15—C1655.4 (2)
C3—C4—C5—C625.1 (3)C14—C15—C16—C1753.7 (3)
N2—C5—C6—C779.1 (2)C15—C16—C17—C1854.3 (2)
C4—C5—C6—C7102.0 (2)C5—N2—C18—C17123.2 (2)
C5—C6—C7—O311.8 (3)C14—N2—C18—C1755.6 (2)
C5—C6—C7—C8168.86 (16)C16—C17—C18—N255.2 (2)
O3—C7—C8—C91.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O3i0.962.483.426 (3)169
C6—H6A···O2ii0.972.463.278 (2)142
C6—H6B···O20.972.312.798 (3)110
C14—H14B···O2ii0.972.523.470 (2)167
C18—H18A···N10.972.683.316 (2)124
C18—H18A···N1iii0.972.663.341 (3)127
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x+1/2, y1/2, z+3/2; (iii) x, y+1, z+2.
(2) Ethyl 2-cyano-5-(4-methoxyphenyl)-5-oxo-3-(piperidin-1-yl)pent-2-enoate top
Crystal data top
C20H24N2O4Dx = 1.332 Mg m3
Mr = 356.41Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3511 reflections
a = 8.3337 (7) Åθ = 2.5–27.3°
b = 8.6333 (7) ŵ = 0.09 mm1
c = 24.7075 (19) ÅT = 293 K
V = 1777.6 (2) Å3Needle, colourless
Z = 40.7 × 0.05 × 0.02 mm
F(000) = 760
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.079
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.5°
φ and ω scansh = 99
11639 measured reflectionsk = 1010
3129 independent reflectionsl = 2928
2295 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.1237P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.20 e Å3
3129 reflectionsΔρmin = 0.19 e Å3
235 parametersAbsolute structure: Flack x parameter determined using 771 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 1.0 (10)
Crystal data top
C20H24N2O4V = 1777.6 (2) Å3
Mr = 356.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.3337 (7) ŵ = 0.09 mm1
b = 8.6333 (7) ÅT = 293 K
c = 24.7075 (19) Å0.7 × 0.05 × 0.02 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2295 reflections with I > 2σ(I)
11639 measured reflectionsRint = 0.079
3129 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.110Δρmax = 0.20 e Å3
S = 1.01Δρmin = 0.19 e Å3
3129 reflectionsAbsolute structure: Flack x parameter determined using 771 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
235 parametersAbsolute structure parameter: 1.0 (10)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1452 (3)0.0333 (3)0.83937 (10)0.0214 (6)
O20.2775 (3)0.0519 (3)0.76611 (10)0.0233 (7)
O30.6921 (3)0.0501 (3)0.77621 (10)0.0218 (6)
O40.6213 (3)0.1266 (3)0.52316 (10)0.0273 (7)
N10.2949 (4)0.0391 (4)0.95301 (14)0.0289 (9)
N20.5965 (3)0.2946 (4)0.87428 (12)0.0190 (8)
C10.0745 (4)0.2096 (5)0.83533 (16)0.0253 (10)
H1A0.14680.26740.81140.038*
H1B0.01470.28220.85820.038*
H1C0.13750.13970.85830.038*
C20.0408 (5)0.1168 (5)0.80185 (15)0.0238 (10)
H2A0.10510.18610.77840.029*
H2B0.01820.04300.77850.029*
C30.2628 (4)0.0492 (5)0.81538 (15)0.0187 (9)
C40.3657 (5)0.1265 (5)0.85582 (14)0.0189 (9)
C50.4927 (4)0.2256 (4)0.84053 (15)0.0181 (9)
C60.5112 (4)0.2627 (5)0.78150 (14)0.0195 (9)
H6A0.56280.36550.77780.023*
H6B0.40350.26910.76470.023*
C70.6105 (4)0.1435 (5)0.75118 (14)0.0181 (9)
C80.6098 (5)0.1457 (5)0.69107 (14)0.0187 (9)
C90.7166 (4)0.0515 (5)0.66302 (15)0.0194 (9)
H90.78920.01200.68270.023*
C100.7189 (4)0.0484 (5)0.60751 (15)0.0227 (9)
H100.79380.01570.58910.027*
C110.6110 (5)0.1396 (5)0.57790 (15)0.0214 (9)
C120.5038 (4)0.2352 (5)0.60516 (15)0.0221 (9)
H120.43040.29780.58550.026*
C130.5045 (4)0.2386 (4)0.66112 (15)0.0187 (9)
H130.43210.30520.67960.022*
C140.7512 (5)0.3630 (5)0.85663 (15)0.0227 (9)
H14A0.76540.46640.87330.027*
H14B0.75180.37570.81680.027*
C150.8881 (4)0.2561 (5)0.87383 (15)0.0272 (10)
H15A0.99180.30360.86350.033*
H15B0.87840.15630.85440.033*
C160.8867 (5)0.2261 (5)0.93501 (15)0.0275 (10)
H16A0.96690.14550.94400.033*
H16B0.91680.32210.95440.033*
C170.7206 (5)0.1731 (5)0.95368 (16)0.0264 (10)
H17A0.69760.06860.93910.032*
H17B0.71760.16740.99370.032*
C180.5946 (4)0.2872 (5)0.93370 (14)0.0209 (9)
H18A0.48710.25420.94630.025*
H18B0.61670.39120.94880.025*
C190.3291 (4)0.0806 (5)0.91015 (17)0.0214 (9)
C200.5072 (5)0.2132 (5)0.49119 (16)0.0318 (11)
H20A0.52710.19420.45270.048*
H20B0.39810.18010.50040.048*
H20C0.51910.32400.49880.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0165 (14)0.0273 (16)0.0205 (14)0.0047 (12)0.0001 (11)0.0033 (13)
O20.0265 (16)0.0264 (17)0.0171 (15)0.0001 (14)0.0004 (11)0.0008 (13)
O30.0206 (15)0.0207 (15)0.0240 (15)0.0032 (13)0.0019 (12)0.0010 (14)
O40.0342 (17)0.0319 (17)0.0159 (15)0.0002 (15)0.0019 (13)0.0002 (13)
N10.031 (2)0.031 (2)0.025 (2)0.0071 (18)0.0021 (16)0.0028 (18)
N20.0209 (18)0.0191 (18)0.0170 (18)0.0001 (15)0.0016 (14)0.0008 (15)
C10.021 (2)0.026 (2)0.028 (2)0.0006 (18)0.0038 (18)0.002 (2)
C20.020 (2)0.026 (2)0.025 (2)0.0024 (19)0.0042 (17)0.003 (2)
C30.017 (2)0.015 (2)0.024 (2)0.0060 (19)0.0004 (17)0.0021 (19)
C40.021 (2)0.018 (2)0.018 (2)0.0010 (18)0.0014 (17)0.0031 (18)
C50.019 (2)0.016 (2)0.019 (2)0.0084 (17)0.0023 (17)0.0006 (18)
C60.019 (2)0.019 (2)0.020 (2)0.0001 (17)0.0013 (17)0.0011 (18)
C70.015 (2)0.018 (2)0.021 (2)0.0047 (19)0.0005 (17)0.0005 (19)
C80.016 (2)0.020 (2)0.019 (2)0.0042 (19)0.0001 (16)0.0013 (18)
C90.018 (2)0.018 (2)0.022 (2)0.0023 (18)0.0014 (17)0.001 (2)
C100.019 (2)0.023 (2)0.026 (2)0.0002 (19)0.0046 (17)0.002 (2)
C110.023 (2)0.021 (2)0.019 (2)0.007 (2)0.0007 (17)0.0017 (19)
C120.023 (2)0.021 (2)0.022 (2)0.0029 (19)0.0026 (17)0.0009 (18)
C130.018 (2)0.017 (2)0.022 (2)0.0016 (17)0.0018 (17)0.0016 (18)
C140.024 (2)0.023 (2)0.021 (2)0.0046 (19)0.0028 (18)0.0005 (19)
C150.017 (2)0.035 (3)0.029 (2)0.002 (2)0.0003 (18)0.004 (2)
C160.030 (2)0.028 (2)0.025 (2)0.004 (2)0.0075 (19)0.0006 (19)
C170.029 (2)0.028 (3)0.023 (2)0.0021 (19)0.0047 (18)0.0022 (19)
C180.022 (2)0.024 (2)0.017 (2)0.004 (2)0.0008 (17)0.0038 (18)
C190.018 (2)0.020 (2)0.026 (2)0.0019 (17)0.0006 (18)0.0050 (19)
C200.043 (3)0.033 (3)0.020 (2)0.000 (2)0.004 (2)0.001 (2)
Geometric parameters (Å, º) top
O1—C31.349 (4)C5—C61.501 (5)
O1—C21.462 (4)C6—C71.519 (5)
O2—C31.224 (4)C7—C81.485 (5)
O3—C71.223 (4)C8—C91.391 (5)
O4—C111.360 (4)C8—C131.400 (5)
O4—C201.445 (5)C9—C101.372 (5)
N1—C191.154 (5)C10—C111.401 (5)
N2—C51.341 (5)C11—C121.391 (5)
N2—C181.470 (4)C12—C131.383 (5)
N2—C141.484 (5)C14—C151.527 (5)
C1—C21.499 (5)C15—C161.534 (5)
C3—C41.476 (5)C16—C171.530 (5)
C4—C51.413 (5)C17—C181.522 (5)
C4—C191.433 (5)
C3—O1—C2114.5 (3)C8—C7—C6118.8 (3)
C11—O4—C20117.4 (3)C9—C8—C13118.2 (3)
C5—N2—C18126.5 (3)C9—C8—C7119.2 (4)
C5—N2—C14123.7 (3)C13—C8—C7122.6 (4)
C18—N2—C14108.7 (3)C10—C9—C8121.2 (4)
O1—C2—C1107.2 (3)C9—C10—C11120.2 (4)
O2—C3—O1121.3 (4)O4—C11—C12124.8 (4)
O2—C3—C4127.4 (4)O4—C11—C10115.6 (4)
O1—C3—C4111.3 (3)C12—C11—C10119.5 (3)
C5—C4—C19125.3 (3)C13—C12—C11119.6 (4)
C5—C4—C3121.9 (3)C12—C13—C8121.3 (4)
C19—C4—C3112.7 (3)N2—C14—C15109.1 (3)
N2—C5—C4125.9 (3)C14—C15—C16111.8 (3)
N2—C5—C6116.3 (3)C17—C16—C15110.8 (3)
C4—C5—C6117.8 (3)C18—C17—C16109.5 (3)
C5—C6—C7113.0 (3)N2—C18—C17110.2 (3)
O3—C7—C8121.1 (3)N1—C19—C4177.0 (4)
O3—C7—C6120.0 (3)
C3—O1—C2—C1176.2 (3)C6—C7—C8—C139.2 (5)
C2—O1—C3—O20.2 (5)C13—C8—C9—C100.3 (6)
C2—O1—C3—C4178.4 (3)C7—C8—C9—C10179.2 (3)
O2—C3—C4—C54.6 (6)C8—C9—C10—C110.9 (6)
O1—C3—C4—C5176.9 (3)C20—O4—C11—C123.1 (6)
O2—C3—C4—C19171.2 (4)C20—O4—C11—C10177.2 (3)
O1—C3—C4—C197.3 (5)C9—C10—C11—O4179.1 (4)
C18—N2—C5—C43.1 (6)C9—C10—C11—C121.2 (6)
C14—N2—C5—C4163.3 (4)O4—C11—C12—C13180.0 (4)
C18—N2—C5—C6174.6 (3)C10—C11—C12—C130.3 (6)
C14—N2—C5—C619.0 (5)C11—C12—C13—C80.9 (6)
C19—C4—C5—N21.4 (6)C9—C8—C13—C121.2 (6)
C3—C4—C5—N2176.7 (3)C7—C8—C13—C12178.3 (3)
C19—C4—C5—C6179.1 (3)C5—N2—C14—C15105.1 (4)
C3—C4—C5—C65.6 (5)C18—N2—C14—C1563.4 (4)
N2—C5—C6—C795.8 (4)N2—C14—C15—C1656.5 (4)
C4—C5—C6—C786.3 (4)C14—C15—C16—C1751.3 (5)
C5—C6—C7—O314.8 (5)C15—C16—C17—C1852.1 (5)
C5—C6—C7—C8166.9 (3)C5—N2—C18—C17101.8 (4)
O3—C7—C8—C97.0 (6)C14—N2—C18—C1766.3 (4)
C6—C7—C8—C9171.3 (3)C16—C17—C18—N260.3 (4)
O3—C7—C8—C13172.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O2i0.992.353.274 (5)154
C2—H2B···O3ii0.992.543.305 (5)133
C14—H14B···O2i0.992.563.452 (5)149
C15—H15B···O30.992.643.413 (5)135
C18—H18A···N10.992.463.325 (5)146
C20—H20C···N1i0.982.703.541 (6)145
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x1, y, z.
(3) Ethyl 5-(4-chlorophenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate top
Crystal data top
C19H21ClN2O3Dx = 1.373 Mg m3
Mr = 360.83Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 6432 reflections
a = 4.9520 (3) Åθ = 2.8–27.6°
b = 13.6151 (7) ŵ = 0.24 mm1
c = 25.8916 (15) ÅT = 293 K
V = 1745.66 (17) Å3Rod, colourless
Z = 40.34 × 0.12 × 0.10 mm
F(000) = 760
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.034
Radiation source: fine-focus sealed tubeθmax = 27.7°, θmin = 2.8°
φ and ω scansh = 66
14442 measured reflectionsk = 1715
4047 independent reflectionsl = 3233
3656 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0548P)2 + 0.1249P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.28 e Å3
4047 reflectionsΔρmin = 0.20 e Å3
310 parametersAbsolute structure: Flack x parameter determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.03 (2)
Crystal data top
C19H21ClN2O3V = 1745.66 (17) Å3
Mr = 360.83Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.9520 (3) ŵ = 0.24 mm1
b = 13.6151 (7) ÅT = 293 K
c = 25.8916 (15) Å0.34 × 0.12 × 0.10 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3656 reflections with I > 2σ(I)
14442 measured reflectionsRint = 0.034
4047 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034All H-atom parameters refined
wR(F2) = 0.084Δρmax = 0.28 e Å3
S = 1.01Δρmin = 0.20 e Å3
4047 reflectionsAbsolute structure: Flack x parameter determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
310 parametersAbsolute structure parameter: 0.03 (2)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.55221 (14)0.33608 (4)0.84527 (2)0.03002 (16)
O10.0274 (3)0.73933 (11)1.10559 (5)0.0210 (3)
O20.1821 (4)0.63433 (12)1.05231 (6)0.0280 (4)
O30.1779 (3)0.40036 (11)1.09061 (6)0.0233 (4)
N10.0022 (4)0.69226 (15)1.22454 (7)0.0271 (5)
N20.5362 (4)0.50367 (12)1.18822 (6)0.0187 (4)
C10.3407 (6)0.86131 (19)1.07896 (9)0.0292 (5)
H1A0.491 (6)0.830 (2)1.0987 (11)0.032 (7)*
H1B0.237 (6)0.9116 (19)1.0997 (10)0.026 (7)*
H1C0.421 (7)0.891 (2)1.0485 (12)0.038 (8)*
C20.1488 (6)0.78452 (18)1.06052 (8)0.0249 (5)
H2A0.002 (6)0.8132 (19)1.0380 (10)0.027 (7)*
H2B0.232 (5)0.734 (2)1.0412 (10)0.024 (7)*
C30.1395 (4)0.66305 (15)1.09611 (8)0.0184 (4)
C40.2456 (4)0.62207 (15)1.14469 (8)0.0173 (4)
C50.4369 (4)0.54647 (14)1.14584 (8)0.0168 (4)
C60.5493 (5)0.51090 (15)1.09470 (8)0.0179 (4)
H6A0.571 (6)0.5688 (18)1.0724 (9)0.021 (6)*
H6B0.731 (6)0.4822 (19)1.0979 (9)0.024 (7)*
C70.3645 (4)0.43913 (15)1.06771 (8)0.0170 (4)
C80.4201 (5)0.41489 (15)1.01243 (8)0.0175 (4)
C90.2544 (5)0.34635 (16)0.98801 (8)0.0220 (5)
H90.110 (6)0.317 (2)1.0070 (11)0.035 (8)*
C100.2952 (5)0.32180 (17)0.93666 (9)0.0250 (5)
H100.192 (6)0.276 (2)0.9204 (10)0.030 (7)*
C110.5024 (5)0.36606 (15)0.90962 (8)0.0221 (5)
C120.6696 (5)0.43409 (18)0.93301 (9)0.0258 (5)
H120.809 (7)0.465 (2)0.9139 (11)0.036 (8)*
C130.6294 (5)0.45836 (18)0.98470 (9)0.0242 (5)
H130.752 (7)0.502 (2)1.0017 (11)0.034 (8)*
C140.6662 (5)0.40587 (16)1.18793 (8)0.0216 (5)
H14A0.686 (5)0.3820 (18)1.1536 (10)0.023 (6)*
H14B0.863 (6)0.4121 (18)1.2002 (10)0.025 (7)*
C150.5062 (6)0.33622 (18)1.22216 (9)0.0276 (5)
H15A0.323 (7)0.327 (2)1.2091 (11)0.033 (7)*
H15B0.589 (7)0.272 (2)1.2214 (10)0.037 (8)*
C160.4846 (6)0.37454 (18)1.27743 (9)0.0270 (5)
H16A0.375 (6)0.332 (2)1.2988 (10)0.029 (7)*
H16B0.660 (7)0.3732 (19)1.2917 (11)0.028 (7)*
C170.3655 (5)0.47757 (19)1.27722 (9)0.0258 (5)
H17A0.159 (6)0.475 (2)1.2673 (11)0.040 (8)*
H17B0.375 (5)0.5059 (18)1.3109 (10)0.025 (7)*
C180.5255 (5)0.54328 (16)1.24127 (8)0.0212 (5)
H18A0.468 (6)0.6078 (19)1.2411 (9)0.020 (6)*
H18B0.710 (6)0.544 (2)1.2521 (10)0.026 (7)*
C190.1157 (4)0.66036 (15)1.18957 (7)0.0180 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0474 (4)0.0284 (3)0.0142 (2)0.0066 (3)0.0048 (2)0.0023 (2)
O10.0276 (8)0.0211 (7)0.0144 (7)0.0060 (7)0.0016 (6)0.0018 (5)
O20.0399 (10)0.0297 (9)0.0145 (7)0.0116 (8)0.0011 (7)0.0007 (6)
O30.0248 (8)0.0243 (8)0.0208 (7)0.0061 (7)0.0065 (7)0.0028 (6)
N10.0281 (12)0.0374 (11)0.0159 (9)0.0058 (9)0.0000 (8)0.0010 (7)
N20.0228 (9)0.0172 (8)0.0161 (8)0.0025 (8)0.0020 (7)0.0016 (6)
C10.0337 (13)0.0316 (13)0.0224 (11)0.0097 (11)0.0030 (11)0.0047 (9)
C20.0349 (13)0.0247 (12)0.0151 (10)0.0068 (10)0.0034 (10)0.0038 (8)
C30.0221 (10)0.0165 (10)0.0168 (9)0.0011 (9)0.0002 (8)0.0008 (8)
C40.0218 (11)0.0159 (9)0.0141 (9)0.0018 (8)0.0013 (8)0.0010 (7)
C50.0178 (10)0.0155 (9)0.0171 (9)0.0057 (8)0.0006 (8)0.0011 (7)
C60.0189 (10)0.0200 (10)0.0148 (9)0.0005 (9)0.0019 (8)0.0007 (8)
C70.0173 (10)0.0165 (10)0.0171 (10)0.0033 (8)0.0008 (8)0.0010 (8)
C80.0191 (10)0.0184 (9)0.0151 (9)0.0049 (8)0.0007 (8)0.0002 (7)
C90.0239 (11)0.0221 (11)0.0199 (10)0.0018 (10)0.0014 (8)0.0011 (9)
C100.0314 (13)0.0223 (12)0.0213 (11)0.0013 (10)0.0025 (10)0.0048 (9)
C110.0301 (13)0.0239 (11)0.0122 (9)0.0111 (9)0.0011 (8)0.0003 (7)
C120.0274 (12)0.0302 (12)0.0199 (11)0.0003 (11)0.0074 (10)0.0001 (9)
C130.0243 (12)0.0282 (12)0.0201 (11)0.0027 (10)0.0025 (9)0.0031 (9)
C140.0255 (12)0.0219 (11)0.0175 (10)0.0075 (9)0.0017 (9)0.0024 (8)
C150.0414 (16)0.0173 (11)0.0243 (11)0.0018 (11)0.0057 (10)0.0008 (8)
C160.0346 (14)0.0260 (11)0.0202 (11)0.0066 (11)0.0012 (11)0.0026 (8)
C170.0224 (12)0.0376 (13)0.0173 (11)0.0024 (10)0.0006 (9)0.0038 (9)
C180.0283 (13)0.0187 (11)0.0168 (10)0.0041 (9)0.0070 (9)0.0036 (8)
C190.0195 (11)0.0199 (10)0.0146 (9)0.0011 (9)0.0030 (7)0.0043 (8)
Geometric parameters (Å, º) top
Cl1—C111.733 (2)C8—C131.393 (3)
O1—C31.350 (3)C9—C101.386 (3)
O1—C21.450 (3)C9—H90.96 (3)
O2—C31.218 (3)C10—C111.381 (3)
O3—C71.218 (3)C10—H100.91 (3)
N1—C191.151 (3)C11—C121.382 (4)
N2—C51.336 (3)C12—C131.393 (3)
N2—C181.477 (2)C12—H120.95 (3)
N2—C141.479 (3)C13—H130.96 (3)
C1—C21.492 (3)C14—C151.521 (3)
C1—H1A1.00 (3)C14—H14A0.95 (3)
C1—H1B1.01 (3)C14—H14B1.03 (3)
C1—H1C0.97 (3)C15—C161.527 (3)
C2—H2A1.01 (3)C15—H15A0.97 (3)
C2—H2B0.95 (3)C15—H15B0.97 (3)
C3—C41.473 (3)C16—C171.522 (4)
C4—C51.399 (3)C16—H16A0.97 (3)
C4—C191.427 (3)C16—H16B0.94 (3)
C5—C61.516 (3)C17—C181.515 (3)
C6—C71.510 (3)C17—H17A1.05 (3)
C6—H6A0.98 (3)C17—H17B0.95 (3)
C6—H6B0.99 (3)C18—H18A0.92 (3)
C7—C81.494 (3)C18—H18B0.95 (3)
C8—C91.394 (3)
C3—O1—C2115.72 (16)C9—C10—H10121.9 (18)
C5—N2—C18126.25 (18)C10—C11—C12121.0 (2)
C5—N2—C14123.27 (17)C10—C11—Cl1119.38 (18)
C18—N2—C14110.45 (16)C12—C11—Cl1119.59 (18)
C2—C1—H1A110.2 (17)C11—C12—C13119.6 (2)
C2—C1—H1B108.7 (17)C11—C12—H12120.4 (17)
H1A—C1—H1B113 (2)C13—C12—H12120.0 (18)
C2—C1—H1C107.0 (19)C12—C13—C8120.1 (2)
H1A—C1—H1C107 (3)C12—C13—H13119.9 (18)
H1B—C1—H1C111 (2)C8—C13—H13119.9 (18)
O1—C2—C1107.71 (18)N2—C14—C15109.4 (2)
O1—C2—H2A109.3 (16)N2—C14—H14A111.0 (15)
C1—C2—H2A111.9 (15)C15—C14—H14A112.6 (16)
O1—C2—H2B107.2 (16)N2—C14—H14B109.7 (15)
C1—C2—H2B113.9 (17)C15—C14—H14B111.4 (15)
H2A—C2—H2B107 (2)H14A—C14—H14B103 (2)
O2—C3—O1121.50 (19)C14—C15—C16111.7 (2)
O2—C3—C4127.7 (2)C14—C15—H15A111.2 (17)
O1—C3—C4110.76 (17)C16—C15—H15A107.8 (17)
C5—C4—C19123.83 (18)C14—C15—H15B109.3 (18)
C5—C4—C3122.57 (18)C16—C15—H15B111.0 (16)
C19—C4—C3113.34 (18)H15A—C15—H15B106 (3)
N2—C5—C4125.98 (18)C17—C16—C15109.80 (19)
N2—C5—C6116.28 (19)C17—C16—H16A109.8 (17)
C4—C5—C6117.72 (18)C15—C16—H16A111.7 (16)
C7—C6—C5112.84 (18)C17—C16—H16B112.1 (17)
C7—C6—H6A108.4 (15)C15—C16—H16B107.3 (17)
C5—C6—H6A107.3 (14)H16A—C16—H16B106 (2)
C7—C6—H6B109.7 (15)C18—C17—C16110.1 (2)
C5—C6—H6B112.9 (15)C18—C17—H17A112.1 (16)
H6A—C6—H6B105 (2)C16—C17—H17A110.3 (17)
O3—C7—C8120.7 (2)C18—C17—H17B107.1 (16)
O3—C7—C6120.99 (18)C16—C17—H17B110.5 (15)
C8—C7—C6118.32 (18)H17A—C17—H17B107 (2)
C9—C8—C13119.25 (19)N2—C18—C17112.00 (18)
C9—C8—C7118.27 (19)N2—C18—H18A110.7 (15)
C13—C8—C7122.5 (2)C17—C18—H18A113.8 (17)
C10—C9—C8120.7 (2)N2—C18—H18B104.0 (16)
C10—C9—H9120.0 (17)C17—C18—H18B108.9 (16)
C8—C9—H9119.2 (17)H18A—C18—H18B107 (2)
C11—C10—C9119.3 (2)N1—C19—C4177.2 (2)
C11—C10—H10118.7 (18)
C3—O1—C2—C1175.7 (2)O3—C7—C8—C13179.3 (2)
C2—O1—C3—O20.5 (3)C6—C7—C8—C132.2 (3)
C2—O1—C3—C4178.83 (19)C13—C8—C9—C100.4 (3)
O2—C3—C4—C56.0 (4)C7—C8—C9—C10179.4 (2)
O1—C3—C4—C5175.76 (19)C8—C9—C10—C110.1 (3)
O2—C3—C4—C19168.3 (2)C9—C10—C11—C120.2 (3)
O1—C3—C4—C199.9 (3)C9—C10—C11—Cl1179.56 (18)
C18—N2—C5—C418.0 (4)C10—C11—C12—C130.2 (4)
C14—N2—C5—C4159.7 (2)Cl1—C11—C12—C13179.89 (18)
C18—N2—C5—C6160.3 (2)C11—C12—C13—C80.6 (4)
C14—N2—C5—C622.0 (3)C9—C8—C13—C120.7 (3)
C19—C4—C5—N24.1 (3)C7—C8—C13—C12179.0 (2)
C3—C4—C5—N2177.9 (2)C5—N2—C14—C15118.5 (2)
C19—C4—C5—C6177.7 (2)C18—N2—C14—C1559.5 (2)
C3—C4—C5—C63.9 (3)N2—C14—C15—C1657.9 (3)
N2—C5—C6—C7100.4 (2)C14—C15—C16—C1755.1 (3)
C4—C5—C6—C781.2 (2)C15—C16—C17—C1853.4 (3)
C5—C6—C7—O314.4 (3)C5—N2—C18—C17117.7 (2)
C5—C6—C7—C8167.06 (18)C14—N2—C18—C1760.2 (3)
O3—C7—C8—C90.5 (3)C16—C17—C18—N256.8 (2)
C6—C7—C8—C9178.07 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O20.98 (3)2.19 (3)2.709 (3)112 (2)
C6—H6B···O3i0.99 (3)2.48 (3)3.459 (3)170 (2)
C15—H15A···Cl1ii0.97 (3)2.95 (3)3.688 (2)133 (2)
C15—H15B···N1iii0.97 (3)2.69 (3)3.417 (3)132 (2)
C18—H18A···N10.92 (3)2.61 (3)3.319 (3)134 (2)
C18—H18B···N1i0.95 (3)2.59 (3)3.142 (3)117 (2)
Symmetry codes: (i) x+1, y, z; (ii) x1/2, y+1/2, z+2; (iii) x+1, y1/2, z+5/2.

Experimental details

(1)(2)(3)
Crystal data
Chemical formulaC19H22N2O3C20H24N2O4C19H21ClN2O3
Mr326.38356.41360.83
Crystal system, space groupMonoclinic, P21/nOrthorhombic, P212121Orthorhombic, P212121
Temperature (K)293293293
a, b, c (Å)12.4152 (10), 8.9071 (6), 16.5072 (12)8.3337 (7), 8.6333 (7), 24.7075 (19)4.9520 (3), 13.6151 (7), 25.8916 (15)
α, β, γ (°)90, 107.194 (2), 9090, 90, 9090, 90, 90
V3)1743.8 (2)1777.6 (2)1745.66 (17)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.090.090.24
Crystal size (mm)0.60 × 0.06 × 0.020.7 × 0.05 × 0.020.34 × 0.12 × 0.10
Data collection
DiffractometerBruker APEXII CCD area-detectorBruker APEXII CCD area-detectorBruker APEXII CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7982, 3550, 2211 11639, 3129, 2295 14442, 4047, 3656
Rint0.0440.0790.034
(sin θ/λ)max1)0.6250.5950.653
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.140, 1.02 0.047, 0.110, 1.01 0.034, 0.084, 1.01
No. of reflections355031294047
No. of parameters217235310
No. of restraints300
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.22, 0.260.20, 0.190.28, 0.20
Absolute structure?Flack x parameter determined using 771 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)Flack x parameter determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter?1.0 (10)0.03 (2)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015).

Hydrogen-bond geometry (Å, º) for (1) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O3i0.962.483.426 (3)169.1
C6—H6A···O2ii0.972.463.278 (2)142.2
C6—H6B···O20.972.312.798 (3)110.2
C14—H14B···O2ii0.972.523.470 (2)166.8
C18—H18A···N10.972.683.316 (2)123.9
C18—H18A···N1iii0.972.663.341 (3)127.3
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x+1/2, y1/2, z+3/2; (iii) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) for (2) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O2i0.992.353.274 (5)154.3
C2—H2B···O3ii0.992.543.305 (5)133.4
C14—H14B···O2i0.992.563.452 (5)149.2
C15—H15B···O30.992.643.413 (5)134.8
C18—H18A···N10.992.463.325 (5)145.9
C20—H20C···N1i0.982.703.541 (6)144.6
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (3) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O20.98 (3)2.19 (3)2.709 (3)112 (2)
C6—H6B···O3i0.99 (3)2.48 (3)3.459 (3)170 (2)
C15—H15A···Cl1ii0.97 (3)2.95 (3)3.688 (2)133 (2)
C15—H15B···N1iii0.97 (3)2.69 (3)3.417 (3)132 (2)
C18—H18A···N10.92 (3)2.61 (3)3.319 (3)134 (2)
C18—H18B···N1i0.95 (3)2.59 (3)3.142 (3)117 (2)
Symmetry codes: (i) x+1, y, z; (ii) x1/2, y+1/2, z+2; (iii) x+1, y1/2, z+5/2.
 

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