organic compounds
4-Cyano-N-ethylspiro[chromene-2,4′-piperidine]-1′-carboxamide
aDepartment of Physics, Thiagarajar College, Madurai 625 009, India
*Correspondence e-mail: vasan692000@yahoo.co.in
The title compound, C17H19N3O2, crystallizes with two independent molecules (A and B) in the In both molecules, the pyran ring has a twisted conformation (5S4), with Q = 0.301 (3) Å, θ = 116.7 (6) and φ= 213.6 (7)° for molecule A, and Q = 0.364 (2) Å, θ = 113.7 (3) and φ = 213.0 (4)° for molecule B. In molecule B, the terminal ethyl group is disordered over two orientations with an occupancy ratio of 0.55 (1):0.45 (1). In the crystal, molecules A and B form very similar but separate R12(7) motifs through N—H⋯O and C—H⋯O hydrogen bonds. The resulting chains along [001] are interlinked by weaker C—H⋯O and C—H⋯π interactions, forming layers parallel to the bc plane.
Related literature
For related structures, see: Rajalakshmi et al. (2012). For their biological activity, see: Kemnitzer et al. (2004); Mahdavi et al. (2011); Patil et al. (2012); Vosooghi et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLUTON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812051124/ld2085sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812051124/ld2085Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812051124/ld2085Isup3.cml
Trimethylsilylcyanide (1.2 mmol) was added to a mixture of N-ethyl-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxamide (1.0 mmol) and catalytic amount of ZnI2 in dichloromethane (10 vol) under a nitrogen atmosphere. The reaction mixture was stirred at 50°C for 6 h and then cooled down to the room temperature; then diluted HCl (5 ml) was added and stirring continued for additional 2 h. The solution was extracted with ethylacetate (20 ml), dried over Na2SO4 and evaporated to dryness. The crude product was dissolved in benzene (10 ml), to which tosic acid (0.1 mmol) had been added, and the solution was heated to reflux for 2 h. After completion of the reaction as indicated by TLC, the reaction mixture was concentrated under reduced pressure. The residue was diluted with ethylacetate (20 ml), washed with bicarbonate solution (10 ml) dried and concentrated. The crude product was purified by
to provide the desired product as colorless solid. Crystals of the title compound were grown from its solution in ethanol by slow evaporation at room temperature.The positions of the hydrogen atoms bound to N3A, C11A, C13A, N3B, C9B and C11B were allowed to refine with isotropic temperature factors since they participate in the hydrogen-bonding. All other hydrogen atoms were included into the model at geometrically calculated positions (C—H target distance 0.96 Å for methyl hydrogen atoms, 0.93 Å for all others) and refined using a riding model with their Uiso constrained to 1.2 times Ueq (1.5 times for methyl H atoms) of the respective atom to which the hydrogen atom binds. The methyl H atoms involving the C16 atom of molecules A and B were allowed to refine with their torsion angles optimized. In molecule B, the terminal ethyl group C15B and C16B is disordered over two sets of sites the treatment of which converged with occupancy values of 0.55 (1) and 0.45 (1) for the major and minor components, respectively.
Chromene with piperidine derivatives are potent agents inducing apoptosis (Kemnitzer et al., 2004). They also exhibit cytotoxic (Vosooghi et al., 2010), antifungal (Mahdavi et al., 2011) and antimycobacterial activities (Patil et al., 2012). In a continuation to our study of the structural features of 1'-benzyl spiro[chromene-2,4'-piperidine]-4-carbonitrile (Rajalakshmi et al., 2012), we report here the
of the title compound: 4-cyano-N-ethylspiro[chromene-2,4'-piperidine]- 1'-carboxamide.The title compound contains two molecules in the
(Fig. 1). The piperidine ring forms dihedral angles of 11.9 (2)° and 78.2 (1)° for molecule A, 7.9 (8)° and 74.3 (1)° for molecule B, with the N-ethyl carboxamide group and chroman ring, respectively. The pyran ring in the molecules A and B (C8/C7/C2/O1/C1/C9) adopts a twisted conformation (5S4) with O1 and C1 atoms deviating respectively from the mean plane defined by the rest of the atoms by -0.1926 (5) Å and 0.2626 (5) Å in molecule A, and by -0.2375 (4) Å and 0.3063 (5) Å in molecule B. The piperidine ring (C1/C10/C11/N2/C12/C13) adopts a chair conformation (1C4) with C1 and N2 atoms deviating respectively from the rest of the atoms by -0.6644 (3) Å and 0.6065 (3) Å in molecule A and by -0.6418 (4) Å and 0.6263 (4)Å in molecule B (Cremer & Pople, 1975). In molecule B, the terminal ethyl group is disordered over two positions with refined occupancy ratios of 0.55 (1):0.45 (1).Molecules A and B form separate chains along [001] through similar R21(7) motifs (Bernstein et al., 1995) through N—H···O and C—H···O hydrogen bonds. The chains made of molecules B form layers parallel to bc plane owing to formation of an additional C9B—H9B···O2B hydrogen bond. The π interaction that appears to be a weaker link between molecules A and B resulting in layers parallel to the (100) plane (Fig.2 and Fig.3).
also has a noteworthy C—H···For related structures, see: Rajalakshmi et al. (2012). For their biological activity, see: Kemnitzer et al. (2004); Mahdavi et al. (2011); Patil et al. (2012); Vosooghi et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLUTON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecules of the title compound with atom-labeling scheme. Displacement ellipsoids are drawn at 30% probability. For the sake of clarity, H atoms are not shown. | |
Fig. 2. Packing diagram of the title compound, showing formation of the separate R21 (7) motifs by molecules A and B (molecules A are shown in red, molecules B - in black). The cyano and ethyl groups were omitted for clarity as well as the H atoms not involved in the hydrogen bonding. | |
Fig. 3. The layers formed by molecules B along (100) plane. Non-essential groups and most hydrogen atoms were omitted for clarity. |
C17H19N3O2 | F(000) = 1264 |
Mr = 297.35 | Dx = 1.228 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5377 reflections |
a = 22.7845 (8) Å | θ = 2–24.5° |
b = 14.3370 (5) Å | µ = 0.08 mm−1 |
c = 9.8442 (3) Å | T = 298 K |
β = 90.783 (1)° | Block, colourless |
V = 3215.42 (19) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 8 |
Bruker Kappa APEXII diffractometer | 5377 independent reflections |
Radiation source: fine-focus sealed tube | 3664 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 24.5°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −26→26 |
Tmin = 0.972, Tmax = 0.980 | k = −16→16 |
26353 measured reflections | l = −11→11 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0985P)2 + 0.7688P] where P = (Fo2 + 2Fc2)/3 |
5377 reflections | (Δ/σ)max < 0.001 |
455 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C17H19N3O2 | V = 3215.42 (19) Å3 |
Mr = 297.35 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 22.7845 (8) Å | µ = 0.08 mm−1 |
b = 14.3370 (5) Å | T = 298 K |
c = 9.8442 (3) Å | 0.35 × 0.30 × 0.25 mm |
β = 90.783 (1)° |
Bruker Kappa APEXII diffractometer | 5377 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | 3664 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.980 | Rint = 0.028 |
26353 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.177 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.29 e Å−3 |
5377 reflections | Δρmin = −0.20 e Å−3 |
455 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 21.7749 (0.0093) x - 3.7501 (0.0221) y + 1.2007 (0.0105) z = 19.0074 (0.0242) * 0.0040 (0.0012) C10B * -0.0040 (0.0012) C11B * 0.0040 (0.0012) C12B * -0.0040 (0.0012) C13B 0.6065 (0.0031) N2B -0.6644 (0.0031) C1B Rms deviation of fitted atoms = 0.0040 - 7.4187 (0.0441) x + 12.7666 (0.0128) y + 3.1729 (0.0124) z = 1.9928 (0.0318) Angle to previous plane (with approximate esd) = 59.92 ( 0.15 ) * -0.0108 (0.0016) C10A * 0.0109 (0.0016) C11A * -0.0109 (0.0016) C12A * 0.0108 (0.0016) C13A -0.6263 (0.0038) N2A 0.6418 (0.0039) C1A Rms deviation of fitted atoms = 0.0109 4.5322 (0.0409) x - 8.3873 (0.0214) y + 7.7125 (0.0087) z = 2.7977 (0.0417) Angle to previous plane (with approximate esd) = 70.38 ( 0.11 ) * 0.0378 (0.0016) C7A * 0.0217 (0.0009) C9A * -0.0402 (0.0017) C8A * -0.0193 (0.0008) C2A 0.2626 (0.0051) C1A -0.1926 (0.0048) O1A Rms deviation of fitted atoms = 0.0312 5.5265 (0.0340) x - 2.7276 (0.0239) y + 9.3313 (0.0033) z = 11.8513 (0.0329) Angle to previous plane (with approximate esd) = 24.84 ( 0.15 ) * 0.0573 (0.0014) C7B * 0.0322 (0.0008) C9B * -0.0600 (0.0015) C8B * -0.0295 (0.0007) C2B 0.3063 (0.0047) C1B -0.2375 (0.0041) O1B Rms deviation of fitted atoms = 0.0469 13.1321 (0.0221) x - 10.5040 (0.0116) y - 3.6406 (0.0129) z = 2.2898 (0.0197) Angle to previous plane (with approximate esd) = 86.26 ( 0.11 ) * 0.2282 (0.0021) C10A * -0.2326 (0.0021) C11A * -0.2132 (0.0023) C12A * 0.2074 (0.0023) C13A * 0.2229 (0.0020) N2A * -0.2128 (0.0019) C1A Rms deviation of fitted atoms = 0.2197 16.1311 (0.0326) x - 9.6533 (0.0246) y - 2.1927 (0.0143) z = 5.2730 (0.0209) Angle to previous plane (with approximate esd) = 11.90 ( 0.24 ) * 0.0010 (0.0008) O2A * -0.0020 (0.0016) C14A * 0.0019 (0.0015) N3A * -0.0009 (0.0007) C15A Rms deviation of fitted atoms = 0.0015 13.1321 (0.0221) x - 10.5040 (0.0116) y - 3.6406 (0.0129) z = 2.2898 (0.0197) Angle to previous plane (with approximate esd) = 11.90 ( 0.24 ) * 0.2282 (0.0021) C10A * -0.2326 (0.0021) C11A * -0.2132 (0.0023) C12A * 0.2074 (0.0023) C13A * 0.2229 (0.0020) N2A * -0.2128 (0.0019) C1A Rms deviation of fitted atoms = 0.2197 4.0940 (0.0233) x - 7.7943 (0.0130) y + 8.0459 (0.0062) z = 3.0223 (0.0189) Angle to previous plane (with approximate esd) = 78.16 ( 0.09 ) * -0.0636 (0.0019) C9A * 0.1923 (0.0017) C1A * -0.0711 (0.0019) C8A * 0.0861 (0.0018) C7A * 0.0441 (0.0018) C2A * -0.1878 (0.0017) O1A Rms deviation of fitted atoms = 0.1229 19.4554 (0.0116) x - 7.4511 (0.0119) y + 0.1595 (0.0105) z = 13.7691 (0.0188) Angle to previous plane (with approximate esd) = 62.69 ( 0.09 ) * 0.2327 (0.0017) C10B * -0.2207 (0.0017) C11B * -0.2127 (0.0017) C12B * 0.2240 (0.0017) C13B * 0.2129 (0.0017) N2B * -0.2363 (0.0016) C1B Rms deviation of fitted atoms = 0.2234 19.0116 (0.1135) x - 7.7504 (0.1004) y - 1.1689 (0.0356) z = 12.1762 (0.2227) Angle to previous plane (with approximate esd) = 7.92 ( 0.76 ) * 0.0316 (0.0019) O2B * -0.0581 (0.0036) C14B * 0.0512 (0.0032) N3B * -0.0247 (0.0015) C15B_a Rms deviation of fitted atoms = 0.0436 19.4554 (0.0116) x - 7.4511 (0.0119) y + 0.1595 (0.0105) z = 13.7691 (0.0188) Angle to previous plane (with approximate esd) = 7.92 ( 0.76 ) * 0.2327 (0.0017) C10B * -0.2207 (0.0017) C11B * -0.2127 (0.0017) C12B * 0.2240 (0.0017) C13B * 0.2129 (0.0017) N2B * -0.2363 (0.0016) C1B Rms deviation of fitted atoms = 0.2234 4.1399 (0.0218) x - 2.4193 (0.0136) y + 9.5114 (0.0026) z = 11.0331 (0.0176) Angle to previous plane (with approximate esd) = 74.34 ( 0.08 ) * -0.0681 (0.0018) C9B * 0.2285 (0.0016) C1B * -0.0966 (0.0017) C8B * 0.1149 (0.0015) C7B * 0.0475 (0.0015) C2B * -0.2262 (0.0014) O1B Rms deviation of fitted atoms = 0.1488 |
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 > σ(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 | Occ. (<1) | |
O1A | 0.64156 (8) | 0.54792 (13) | 0.5566 (2) | 0.0827 (6) | |
O2A | 0.54458 (9) | 0.21606 (13) | 0.64983 (17) | 0.0765 (5) | |
N1A | 0.86504 (18) | 0.6414 (3) | 0.5007 (5) | 0.1602 (17) | |
N2A | 0.59436 (10) | 0.32206 (14) | 0.52456 (19) | 0.0636 (6) | |
N3A | 0.52207 (10) | 0.22847 (16) | 0.4292 (2) | 0.0679 (6) | |
C1A | 0.67909 (12) | 0.47355 (17) | 0.5127 (3) | 0.0631 (7) | |
C2A | 0.66403 (15) | 0.61628 (18) | 0.6402 (3) | 0.0770 (8) | |
C3A | 0.62636 (19) | 0.6657 (2) | 0.7180 (3) | 0.1049 (11) | |
H3A | 0.5868 | 0.6498 | 0.7208 | 0.126* | |
C4A | 0.6473 (3) | 0.7387 (3) | 0.7913 (4) | 0.1313 (18) | |
C5A | 0.7030 (4) | 0.7632 (3) | 0.7908 (5) | 0.150 (2) | |
H5A | 0.7155 | 0.8143 | 0.8418 | 0.179* | |
C6A | 0.7447 (2) | 0.7118 (2) | 0.7122 (4) | 0.1209 (16) | |
H6A | 0.7843 | 0.7279 | 0.7130 | 0.145* | |
C7A | 0.72431 (15) | 0.63792 (17) | 0.6358 (3) | 0.0767 (9) | |
C8A | 0.75991 (13) | 0.5822 (2) | 0.5441 (3) | 0.0773 (8) | |
C9A | 0.73837 (15) | 0.5081 (2) | 0.4842 (3) | 0.0775 (8) | |
C10A | 0.64728 (14) | 0.43474 (18) | 0.3889 (3) | 0.0733 (8) | |
H10A | 0.6423 | 0.4842 | 0.3225 | 0.088* | |
H10B | 0.6714 | 0.3866 | 0.3485 | 0.088* | |
C11A | 0.58882 (14) | 0.3948 (2) | 0.4199 (3) | 0.0722 (8) | |
C12A | 0.62276 (14) | 0.3556 (2) | 0.6501 (3) | 0.0826 (9) | |
H12A | 0.6278 | 0.3039 | 0.7127 | 0.099* | |
H12B | 0.5978 | 0.4015 | 0.6927 | 0.099* | |
C13A | 0.68102 (13) | 0.3981 (2) | 0.6220 (3) | 0.0744 (8) | |
H13A | 0.7077 | 0.3493 | 0.5939 | 0.089* | |
H13B | 0.6966 | 0.4250 | 0.7054 | 0.089* | |
C14A | 0.55232 (11) | 0.25439 (16) | 0.5395 (2) | 0.0550 (6) | |
C15A | 0.47839 (14) | 0.1548 (2) | 0.4335 (3) | 0.0863 (9) | |
H15A | 0.4797 | 0.1262 | 0.5228 | 0.104* | |
H15B | 0.4398 | 0.1823 | 0.4210 | 0.104* | |
C16A | 0.48610 (19) | 0.0829 (3) | 0.3323 (5) | 0.1428 (18) | |
H16A | 0.4825 | 0.1098 | 0.2433 | 0.214* | |
H16B | 0.4566 | 0.0358 | 0.3432 | 0.214* | |
H16C | 0.5243 | 0.0554 | 0.3433 | 0.214* | |
C17A | 0.81935 (18) | 0.6132 (3) | 0.5193 (4) | 0.1113 (13) | |
O1B | 0.82241 (6) | 0.54557 (10) | 0.91701 (17) | 0.0585 (4) | |
O2B | 1.00094 (7) | 0.69692 (11) | 1.21492 (17) | 0.0658 (5) | |
N1B | 0.78919 (13) | 0.18872 (18) | 0.8024 (3) | 0.1075 (10) | |
N2B | 0.95277 (8) | 0.63343 (12) | 1.03499 (18) | 0.0512 (5) | |
N3B | 1.01500 (10) | 0.75979 (14) | 1.0100 (3) | 0.0654 (6) | |
C1B | 0.87563 (9) | 0.48999 (15) | 0.9275 (2) | 0.0506 (6) | |
C2B | 0.77116 (9) | 0.50472 (16) | 0.9577 (2) | 0.0509 (6) | |
C3B | 0.72738 (11) | 0.56214 (19) | 1.0024 (3) | 0.0669 (7) | |
H3B | 0.7337 | 0.6260 | 1.0106 | 0.080* | |
C4B | 0.67375 (12) | 0.5239 (2) | 1.0350 (3) | 0.0795 (8) | |
H4B | 0.6438 | 0.5626 | 1.0645 | 0.095* | |
C5B | 0.66405 (12) | 0.4301 (2) | 1.0248 (3) | 0.0782 (8) | |
H5B | 0.6279 | 0.4052 | 1.0482 | 0.094* | |
C6B | 0.70809 (11) | 0.37264 (19) | 0.9795 (2) | 0.0649 (7) | |
H6B | 0.7015 | 0.3088 | 0.9723 | 0.078* | |
C7B | 0.76231 (9) | 0.40935 (16) | 0.9444 (2) | 0.0523 (6) | |
C8B | 0.81077 (10) | 0.35561 (16) | 0.8874 (3) | 0.0594 (6) | |
C9B | 0.86373 (11) | 0.39305 (17) | 0.8769 (3) | 0.0617 (7) | |
C10B | 0.91981 (10) | 0.54055 (15) | 0.8409 (2) | 0.0536 (6) | |
H10C | 0.9046 | 0.5451 | 0.7486 | 0.064* | |
H10D | 0.9559 | 0.5046 | 0.8387 | 0.064* | |
C11B | 0.93324 (12) | 0.63759 (17) | 0.8938 (2) | 0.0545 (6) | |
C12B | 0.91192 (11) | 0.58582 (17) | 1.1254 (2) | 0.0606 (6) | |
H12C | 0.8760 | 0.6218 | 1.1315 | 0.073* | |
H12D | 0.9292 | 0.5815 | 1.2157 | 0.073* | |
C13B | 0.89774 (10) | 0.48906 (16) | 1.0738 (2) | 0.0583 (6) | |
H13C | 0.8681 | 0.4614 | 1.1309 | 0.070* | |
H13D | 0.9327 | 0.4506 | 1.0802 | 0.070* | |
C14B | 0.98940 (9) | 0.69875 (14) | 1.0919 (2) | 0.0485 (5) | |
C15B | 1.0460 (8) | 0.8346 (14) | 1.0830 (13) | 0.070 (3) | 0.550 (10) |
H15C | 1.0681 | 0.8097 | 1.1597 | 0.083* | 0.550 (10) |
H15D | 1.0185 | 0.8808 | 1.1158 | 0.083* | 0.550 (10) |
C16B | 1.0868 (4) | 0.8769 (6) | 0.9786 (7) | 0.116 (4) | 0.550 (10) |
H16D | 1.0641 | 0.9003 | 0.9031 | 0.175* | 0.550 (10) |
H16E | 1.1135 | 0.8300 | 0.9473 | 0.175* | 0.550 (10) |
H16F | 1.1086 | 0.9271 | 1.0195 | 0.175* | 0.550 (10) |
C15C | 1.0598 (9) | 0.8312 (15) | 1.0386 (15) | 0.066 (4) | 0.450 (10) |
H15E | 1.0775 | 0.8203 | 1.1274 | 0.079* | 0.450 (10) |
H15F | 1.0905 | 0.8279 | 0.9713 | 0.079* | 0.450 (10) |
C16C | 1.0324 (5) | 0.9228 (5) | 1.0349 (9) | 0.106 (4) | 0.450 (10) |
H16G | 1.0608 | 0.9694 | 1.0601 | 0.159* | 0.450 (10) |
H16H | 1.0005 | 0.9243 | 1.0975 | 0.159* | 0.450 (10) |
H16I | 1.0179 | 0.9353 | 0.9448 | 0.159* | 0.450 (10) |
C17B | 0.79915 (12) | 0.2625 (2) | 0.8393 (3) | 0.0758 (8) | |
H9A | 0.7620 (14) | 0.477 (2) | 0.420 (4) | 0.101 (11)* | |
H1N3 | 0.5307 (12) | 0.2494 (18) | 0.356 (3) | 0.066 (8)* | |
H4A | 0.6205 (17) | 0.779 (3) | 0.852 (4) | 0.133 (13)* | |
H11A | 0.5669 (13) | 0.455 (2) | 0.456 (3) | 0.093 (9)* | |
H11B | 0.5679 (12) | 0.3651 (18) | 0.341 (3) | 0.081 (8)* | |
H2N3 | 1.0026 (10) | 0.7676 (16) | 0.932 (3) | 0.052 (7)* | |
H9B | 0.8947 (12) | 0.3614 (18) | 0.840 (3) | 0.072 (8)* | |
H11C | 0.9634 (12) | 0.6634 (17) | 0.839 (3) | 0.069 (7)* | |
H11D | 0.8987 (11) | 0.6814 (17) | 0.889 (2) | 0.061 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0796 (13) | 0.0716 (12) | 0.0965 (15) | 0.0050 (9) | −0.0153 (10) | −0.0284 (10) |
O2A | 0.1061 (15) | 0.0809 (12) | 0.0426 (10) | −0.0100 (10) | 0.0012 (9) | 0.0106 (8) |
N1A | 0.112 (3) | 0.164 (4) | 0.204 (4) | −0.044 (3) | −0.022 (3) | 0.075 (3) |
N2A | 0.0885 (15) | 0.0635 (12) | 0.0384 (10) | −0.0106 (11) | −0.0159 (10) | 0.0057 (9) |
N3A | 0.0779 (15) | 0.0810 (15) | 0.0448 (13) | −0.0190 (12) | −0.0040 (11) | 0.0060 (11) |
C1A | 0.0778 (17) | 0.0551 (14) | 0.0563 (15) | 0.0037 (12) | −0.0063 (13) | −0.0072 (11) |
C2A | 0.118 (3) | 0.0527 (15) | 0.0595 (16) | 0.0125 (16) | −0.0162 (16) | −0.0056 (12) |
C3A | 0.152 (3) | 0.076 (2) | 0.087 (2) | 0.030 (2) | −0.013 (2) | −0.0171 (18) |
C4A | 0.235 (6) | 0.072 (3) | 0.086 (3) | 0.027 (3) | −0.034 (3) | −0.025 (2) |
C5A | 0.295 (8) | 0.065 (2) | 0.087 (3) | −0.026 (4) | −0.059 (4) | −0.017 (2) |
C6A | 0.205 (4) | 0.071 (2) | 0.086 (2) | −0.043 (3) | −0.057 (3) | 0.0088 (19) |
C7A | 0.120 (3) | 0.0477 (15) | 0.0611 (17) | −0.0121 (15) | −0.0343 (17) | 0.0111 (12) |
C8A | 0.091 (2) | 0.0588 (16) | 0.081 (2) | −0.0131 (15) | −0.0197 (16) | 0.0239 (15) |
C9A | 0.092 (2) | 0.0634 (18) | 0.077 (2) | −0.0001 (16) | 0.0027 (17) | 0.0111 (15) |
C10A | 0.112 (2) | 0.0593 (15) | 0.0487 (15) | −0.0092 (15) | −0.0067 (14) | 0.0058 (11) |
C11A | 0.107 (2) | 0.0584 (16) | 0.0508 (15) | −0.0139 (16) | −0.0289 (15) | 0.0066 (12) |
C12A | 0.099 (2) | 0.104 (2) | 0.0443 (14) | −0.0282 (17) | −0.0189 (14) | 0.0074 (14) |
C13A | 0.0867 (19) | 0.0840 (18) | 0.0522 (15) | −0.0136 (15) | −0.0161 (13) | 0.0115 (13) |
C14A | 0.0685 (15) | 0.0546 (13) | 0.0419 (13) | 0.0066 (11) | 0.0011 (11) | 0.0011 (10) |
C15A | 0.083 (2) | 0.103 (2) | 0.0737 (19) | −0.0332 (17) | −0.0007 (15) | 0.0026 (17) |
C16A | 0.120 (3) | 0.124 (3) | 0.186 (5) | −0.062 (3) | 0.051 (3) | −0.057 (3) |
C17A | 0.102 (3) | 0.103 (3) | 0.128 (3) | −0.022 (2) | −0.021 (2) | 0.048 (2) |
O1B | 0.0451 (9) | 0.0468 (9) | 0.0835 (12) | 0.0008 (7) | −0.0023 (8) | 0.0072 (8) |
O2B | 0.0766 (12) | 0.0687 (11) | 0.0517 (11) | 0.0012 (8) | −0.0092 (8) | −0.0092 (8) |
N1B | 0.109 (2) | 0.0665 (17) | 0.146 (3) | −0.0219 (15) | −0.0115 (18) | −0.0188 (16) |
N2B | 0.0563 (11) | 0.0536 (11) | 0.0437 (10) | −0.0097 (8) | 0.0004 (9) | −0.0001 (8) |
N3B | 0.0703 (14) | 0.0572 (13) | 0.0681 (15) | −0.0167 (10) | −0.0219 (12) | 0.0083 (11) |
C1B | 0.0402 (11) | 0.0490 (12) | 0.0626 (15) | −0.0002 (9) | −0.0025 (10) | 0.0007 (10) |
C2B | 0.0428 (12) | 0.0586 (14) | 0.0512 (13) | −0.0002 (10) | −0.0053 (10) | 0.0092 (10) |
C3B | 0.0570 (15) | 0.0717 (16) | 0.0721 (17) | 0.0086 (12) | 0.0044 (13) | 0.0073 (13) |
C4B | 0.0570 (17) | 0.103 (2) | 0.079 (2) | 0.0101 (15) | 0.0143 (14) | 0.0103 (17) |
C5B | 0.0547 (16) | 0.110 (2) | 0.0702 (18) | −0.0109 (16) | 0.0091 (14) | 0.0177 (16) |
C6B | 0.0627 (16) | 0.0757 (17) | 0.0560 (15) | −0.0176 (13) | −0.0053 (12) | 0.0149 (12) |
C7B | 0.0498 (13) | 0.0591 (14) | 0.0476 (13) | −0.0053 (11) | −0.0102 (10) | 0.0085 (10) |
C8B | 0.0592 (15) | 0.0477 (13) | 0.0709 (16) | −0.0048 (11) | −0.0127 (12) | 0.0031 (11) |
C9B | 0.0483 (14) | 0.0514 (14) | 0.0853 (19) | 0.0042 (11) | −0.0031 (13) | −0.0038 (12) |
C10B | 0.0497 (13) | 0.0592 (14) | 0.0517 (13) | −0.0053 (10) | −0.0033 (10) | −0.0056 (10) |
C11B | 0.0581 (15) | 0.0580 (15) | 0.0473 (14) | −0.0105 (12) | −0.0012 (12) | 0.0026 (10) |
C12B | 0.0589 (14) | 0.0733 (16) | 0.0498 (14) | −0.0075 (12) | 0.0068 (11) | 0.0032 (11) |
C13B | 0.0517 (13) | 0.0593 (14) | 0.0640 (16) | −0.0062 (11) | 0.0015 (11) | 0.0127 (11) |
C14B | 0.0501 (12) | 0.0438 (12) | 0.0517 (14) | 0.0066 (10) | −0.0043 (10) | −0.0042 (10) |
C15B | 0.075 (8) | 0.071 (4) | 0.063 (7) | −0.024 (5) | −0.001 (5) | 0.005 (6) |
C16B | 0.129 (7) | 0.128 (6) | 0.092 (5) | −0.075 (6) | −0.017 (5) | 0.023 (4) |
C15C | 0.069 (9) | 0.070 (6) | 0.058 (9) | −0.028 (6) | −0.003 (6) | 0.011 (7) |
C16C | 0.142 (9) | 0.063 (5) | 0.114 (7) | −0.022 (5) | 0.008 (6) | −0.008 (4) |
C17B | 0.0683 (17) | 0.0597 (17) | 0.099 (2) | −0.0108 (13) | −0.0089 (15) | −0.0035 (15) |
O1A—C2A | 1.374 (3) | N2B—C14B | 1.369 (3) |
O1A—C1A | 1.437 (3) | N2B—C11B | 1.455 (3) |
O2A—C14A | 1.232 (3) | N2B—C12B | 1.465 (3) |
N1A—C17A | 1.134 (4) | N3B—C14B | 1.330 (3) |
N2A—C14A | 1.373 (3) | N3B—C15B | 1.466 (19) |
N2A—C12A | 1.468 (3) | N3B—C15C | 1.47 (2) |
N2A—C11A | 1.470 (3) | N3B—H2N3 | 0.83 (2) |
N3A—C14A | 1.331 (3) | C1B—C9B | 1.500 (3) |
N3A—C15A | 1.452 (4) | C1B—C10B | 1.513 (3) |
N3A—H1N3 | 0.81 (3) | C1B—C13B | 1.519 (3) |
C1A—C9A | 1.469 (4) | C2B—C3B | 1.371 (3) |
C1A—C10A | 1.516 (3) | C2B—C7B | 1.388 (3) |
C1A—C13A | 1.526 (4) | C3B—C4B | 1.381 (4) |
C2A—C3A | 1.358 (4) | C3B—H3B | 0.9300 |
C2A—C7A | 1.409 (4) | C4B—C5B | 1.365 (4) |
C3A—C4A | 1.354 (6) | C4B—H4B | 0.9300 |
C3A—H3A | 0.9300 | C5B—C6B | 1.378 (4) |
C4A—C5A | 1.318 (8) | C5B—H5B | 0.9300 |
C4A—H4A | 1.03 (4) | C6B—C7B | 1.391 (3) |
C5A—C6A | 1.437 (8) | C6B—H6B | 0.9300 |
C5A—H5A | 0.9300 | C7B—C8B | 1.464 (3) |
C6A—C7A | 1.377 (4) | C8B—C9B | 1.326 (3) |
C6A—H6A | 0.9300 | C8B—C17B | 1.440 (4) |
C7A—C8A | 1.459 (4) | C9B—H9B | 0.92 (3) |
C8A—C9A | 1.307 (4) | C10B—C11B | 1.515 (3) |
C8A—C17A | 1.449 (5) | C10B—H10C | 0.9700 |
C9A—H9A | 0.94 (3) | C10B—H10D | 0.9700 |
C10A—C11A | 1.486 (4) | C11B—H11C | 0.95 (3) |
C10A—H10A | 0.9700 | C11B—H11D | 1.01 (2) |
C10A—H10B | 0.9700 | C12B—C13B | 1.511 (3) |
C11A—H11A | 1.06 (3) | C12B—H12C | 0.9700 |
C11A—H11B | 1.00 (3) | C12B—H12D | 0.9700 |
C12A—C13A | 1.490 (4) | C13B—H13C | 0.9700 |
C12A—H12A | 0.9700 | C13B—H13D | 0.9700 |
C12A—H12B | 0.9700 | C15B—C16B | 1.522 (14) |
C13A—H13A | 0.9700 | C15B—H15C | 0.9700 |
C13A—H13B | 0.9700 | C15B—H15D | 0.9700 |
C15A—C16A | 1.446 (5) | C16B—H16D | 0.9600 |
C15A—H15A | 0.9700 | C16B—H16E | 0.9600 |
C15A—H15B | 0.9700 | C16B—H16F | 0.9600 |
C16A—H16A | 0.9600 | C15C—C16C | 1.46 (2) |
C16A—H16B | 0.9600 | C15C—H15E | 0.9700 |
C16A—H16C | 0.9600 | C15C—H15F | 0.9700 |
O1B—C2B | 1.371 (3) | C16C—H16G | 0.9600 |
O1B—C1B | 1.454 (2) | C16C—H16H | 0.9600 |
O2B—C14B | 1.236 (3) | C16C—H16I | 0.9600 |
N1B—C17B | 1.140 (3) | ||
C2A—O1A—C1A | 119.4 (2) | C14B—N3B—C15B | 113.3 (5) |
C14A—N2A—C12A | 116.2 (2) | C14B—N3B—C15C | 130.6 (6) |
C14A—N2A—C11A | 121.5 (2) | C14B—N3B—H2N3 | 120.6 (16) |
C12A—N2A—C11A | 113.0 (2) | C15B—N3B—H2N3 | 121.0 (17) |
C14A—N3A—C15A | 121.8 (2) | C15C—N3B—H2N3 | 108.1 (18) |
C14A—N3A—H1N3 | 120 (2) | O1B—C1B—C9B | 109.72 (17) |
C15A—N3A—H1N3 | 118.2 (19) | O1B—C1B—C10B | 104.95 (17) |
O1A—C1A—C9A | 111.1 (2) | C9B—C1B—C10B | 112.0 (2) |
O1A—C1A—C10A | 103.6 (2) | O1B—C1B—C13B | 109.74 (18) |
C9A—C1A—C10A | 113.6 (2) | C9B—C1B—C13B | 111.29 (19) |
O1A—C1A—C13A | 109.0 (2) | C10B—C1B—C13B | 108.90 (17) |
C9A—C1A—C13A | 110.8 (2) | C3B—C2B—O1B | 117.6 (2) |
C10A—C1A—C13A | 108.4 (2) | C3B—C2B—C7B | 121.1 (2) |
C3A—C2A—O1A | 118.5 (3) | O1B—C2B—C7B | 121.1 (2) |
C3A—C2A—C7A | 121.8 (3) | C2B—C3B—C4B | 119.1 (3) |
O1A—C2A—C7A | 119.6 (3) | C2B—C3B—H3B | 120.5 |
C4A—C3A—C2A | 118.9 (5) | C4B—C3B—H3B | 120.5 |
C4A—C3A—H3A | 120.6 | C5B—C4B—C3B | 121.1 (3) |
C2A—C3A—H3A | 120.6 | C5B—C4B—H4B | 119.5 |
C5A—C4A—C3A | 122.5 (5) | C3B—C4B—H4B | 119.5 |
C5A—C4A—H4A | 116 (2) | C4B—C5B—C6B | 119.7 (3) |
C3A—C4A—H4A | 122 (3) | C4B—C5B—H5B | 120.2 |
C4A—C5A—C6A | 120.6 (4) | C6B—C5B—H5B | 120.2 |
C4A—C5A—H5A | 119.7 | C5B—C6B—C7B | 120.5 (3) |
C6A—C5A—H5A | 119.7 | C5B—C6B—H6B | 119.8 |
C7A—C6A—C5A | 117.9 (4) | C7B—C6B—H6B | 119.8 |
C7A—C6A—H6A | 121.0 | C2B—C7B—C6B | 118.5 (2) |
C5A—C6A—H6A | 121.0 | C2B—C7B—C8B | 116.42 (19) |
C6A—C7A—C2A | 118.3 (4) | C6B—C7B—C8B | 125.0 (2) |
C6A—C7A—C8A | 124.9 (4) | C9B—C8B—C17B | 120.9 (2) |
C2A—C7A—C8A | 116.7 (2) | C9B—C8B—C7B | 120.6 (2) |
C9A—C8A—C17A | 121.3 (4) | C17B—C8B—C7B | 118.5 (2) |
C9A—C8A—C7A | 121.0 (3) | C8B—C9B—C1B | 120.6 (2) |
C17A—C8A—C7A | 117.7 (3) | C8B—C9B—H9B | 122.4 (16) |
C8A—C9A—C1A | 121.9 (3) | C1B—C9B—H9B | 117.0 (16) |
C8A—C9A—H9A | 118 (2) | C1B—C10B—C11B | 112.3 (2) |
C1A—C9A—H9A | 120 (2) | C1B—C10B—H10C | 109.1 |
C11A—C10A—C1A | 113.4 (2) | C11B—C10B—H10C | 109.1 |
C11A—C10A—H10A | 108.9 | C1B—C10B—H10D | 109.1 |
C1A—C10A—H10A | 108.9 | C11B—C10B—H10D | 109.1 |
C11A—C10A—H10B | 108.9 | H10C—C10B—H10D | 107.9 |
C1A—C10A—H10B | 108.9 | N2B—C11B—C10B | 110.37 (19) |
H10A—C10A—H10B | 107.7 | N2B—C11B—H11C | 110.2 (15) |
N2A—C11A—C10A | 110.4 (2) | C10B—C11B—H11C | 107.7 (15) |
N2A—C11A—H11A | 112.2 (16) | N2B—C11B—H11D | 107.3 (13) |
C10A—C11A—H11A | 100.4 (16) | C10B—C11B—H11D | 113.7 (13) |
N2A—C11A—H11B | 106.1 (15) | H11C—C11B—H11D | 107 (2) |
C10A—C11A—H11B | 115.1 (15) | N2B—C12B—C13B | 110.99 (19) |
H11A—C11A—H11B | 113 (2) | N2B—C12B—H12C | 109.4 |
N2A—C12A—C13A | 111.2 (2) | C13B—C12B—H12C | 109.4 |
N2A—C12A—H12A | 109.4 | N2B—C12B—H12D | 109.4 |
C13A—C12A—H12A | 109.4 | C13B—C12B—H12D | 109.4 |
N2A—C12A—H12B | 109.4 | H12C—C12B—H12D | 108.0 |
C13A—C12A—H12B | 109.4 | C12B—C13B—C1B | 112.18 (19) |
H12A—C12A—H12B | 108.0 | C12B—C13B—H13C | 109.2 |
C12A—C13A—C1A | 113.8 (2) | C1B—C13B—H13C | 109.2 |
C12A—C13A—H13A | 108.8 | C12B—C13B—H13D | 109.2 |
C1A—C13A—H13A | 108.8 | C1B—C13B—H13D | 109.2 |
C12A—C13A—H13B | 108.8 | H13C—C13B—H13D | 107.9 |
C1A—C13A—H13B | 108.8 | O2B—C14B—N3B | 121.2 (2) |
H13A—C13A—H13B | 107.7 | O2B—C14B—N2B | 120.5 (2) |
O2A—C14A—N3A | 121.0 (2) | N3B—C14B—N2B | 118.1 (2) |
O2A—C14A—N2A | 121.2 (2) | N3B—C15B—C16B | 104.8 (8) |
N3A—C14A—N2A | 117.7 (2) | N3B—C15B—H15C | 110.8 |
C16A—C15A—N3A | 114.1 (3) | C16B—C15B—H15C | 110.8 |
C16A—C15A—H15A | 108.7 | N3B—C15B—H15D | 110.8 |
N3A—C15A—H15A | 108.7 | C16B—C15B—H15D | 110.8 |
C16A—C15A—H15B | 108.7 | H15C—C15B—H15D | 108.9 |
N3A—C15A—H15B | 108.7 | C16C—C15C—N3B | 109.1 (14) |
H15A—C15A—H15B | 107.6 | C16C—C15C—H15E | 109.9 |
C15A—C16A—H16A | 109.5 | N3B—C15C—H15E | 109.9 |
C15A—C16A—H16B | 109.5 | C16C—C15C—H15F | 109.9 |
H16A—C16A—H16B | 109.5 | N3B—C15C—H15F | 109.9 |
C15A—C16A—H16C | 109.5 | H15E—C15C—H15F | 108.3 |
H16A—C16A—H16C | 109.5 | C15C—C16C—H16G | 109.5 |
H16B—C16A—H16C | 109.5 | C15C—C16C—H16H | 109.5 |
N1A—C17A—C8A | 177.0 (5) | H16G—C16C—H16H | 109.5 |
C2B—O1B—C1B | 117.26 (16) | C15C—C16C—H16I | 109.5 |
C14B—N2B—C11B | 122.66 (18) | H16G—C16C—H16I | 109.5 |
C14B—N2B—C12B | 117.30 (18) | H16H—C16C—H16I | 109.5 |
C11B—N2B—C12B | 114.26 (18) | N1B—C17B—C8B | 178.9 (4) |
C2A—O1A—C1A—C9A | −38.2 (3) | C1B—O1B—C2B—C3B | 153.4 (2) |
C2A—O1A—C1A—C10A | −160.6 (2) | C1B—O1B—C2B—C7B | −31.4 (3) |
C2A—O1A—C1A—C13A | 84.2 (3) | O1B—C2B—C3B—C4B | 175.5 (2) |
C1A—O1A—C2A—C3A | −157.3 (3) | C7B—C2B—C3B—C4B | 0.3 (4) |
C1A—O1A—C2A—C7A | 27.4 (4) | C2B—C3B—C4B—C5B | 0.7 (4) |
O1A—C2A—C3A—C4A | −174.1 (3) | C3B—C4B—C5B—C6B | −0.8 (4) |
C7A—C2A—C3A—C4A | 1.1 (5) | C4B—C5B—C6B—C7B | 0.1 (4) |
C2A—C3A—C4A—C5A | −0.5 (6) | C3B—C2B—C7B—C6B | −1.0 (3) |
C3A—C4A—C5A—C6A | −0.8 (7) | O1B—C2B—C7B—C6B | −176.04 (19) |
C4A—C5A—C6A—C7A | 1.4 (6) | C3B—C2B—C7B—C8B | 176.1 (2) |
C5A—C6A—C7A—C2A | −0.8 (4) | O1B—C2B—C7B—C8B | 1.1 (3) |
C5A—C6A—C7A—C8A | 176.1 (3) | C5B—C6B—C7B—C2B | 0.8 (3) |
C3A—C2A—C7A—C6A | −0.4 (4) | C5B—C6B—C7B—C8B | −176.0 (2) |
O1A—C2A—C7A—C6A | 174.7 (2) | C2B—C7B—C8B—C9B | 13.7 (3) |
C3A—C2A—C7A—C8A | −177.5 (3) | C6B—C7B—C8B—C9B | −169.4 (2) |
O1A—C2A—C7A—C8A | −2.4 (4) | C2B—C7B—C8B—C17B | −164.4 (2) |
C6A—C7A—C8A—C9A | 173.9 (3) | C6B—C7B—C8B—C17B | 12.5 (4) |
C2A—C7A—C8A—C9A | −9.2 (4) | C17B—C8B—C9B—C1B | −179.8 (2) |
C6A—C7A—C8A—C17A | −7.6 (4) | C7B—C8B—C9B—C1B | 2.1 (4) |
C2A—C7A—C8A—C17A | 169.3 (2) | O1B—C1B—C9B—C8B | −29.7 (3) |
C17A—C8A—C9A—C1A | 177.4 (3) | C10B—C1B—C9B—C8B | −145.8 (2) |
C7A—C8A—C9A—C1A | −4.2 (4) | C13B—C1B—C9B—C8B | 92.0 (3) |
O1A—C1A—C9A—C8A | 26.8 (4) | O1B—C1B—C10B—C11B | 62.5 (2) |
C10A—C1A—C9A—C8A | 143.1 (3) | C9B—C1B—C10B—C11B | −178.47 (19) |
C13A—C1A—C9A—C8A | −94.6 (3) | C13B—C1B—C10B—C11B | −54.9 (2) |
O1A—C1A—C10A—C11A | −62.8 (3) | C14B—N2B—C11B—C10B | 152.5 (2) |
C9A—C1A—C10A—C11A | 176.5 (2) | C12B—N2B—C11B—C10B | −55.1 (3) |
C13A—C1A—C10A—C11A | 52.8 (3) | C1B—C10B—C11B—N2B | 55.4 (3) |
C14A—N2A—C11A—C10A | −158.1 (2) | C14B—N2B—C12B—C13B | −151.31 (19) |
C12A—N2A—C11A—C10A | 56.5 (3) | C11B—N2B—C12B—C13B | 54.7 (3) |
C1A—C10A—C11A—N2A | −56.3 (3) | N2B—C12B—C13B—C1B | −53.9 (3) |
C14A—N2A—C12A—C13A | 157.7 (2) | O1B—C1B—C13B—C12B | −60.2 (2) |
C11A—N2A—C12A—C13A | −54.9 (3) | C9B—C1B—C13B—C12B | 178.10 (19) |
N2A—C12A—C13A—C1A | 52.8 (3) | C10B—C1B—C13B—C12B | 54.1 (2) |
O1A—C1A—C13A—C12A | 61.0 (3) | C15B—N3B—C14B—O2B | −13.1 (8) |
C9A—C1A—C13A—C12A | −176.4 (3) | C15C—N3B—C14B—O2B | 1.9 (11) |
C10A—C1A—C13A—C12A | −51.0 (3) | C15B—N3B—C14B—N2B | 171.4 (8) |
C15A—N3A—C14A—O2A | 0.5 (4) | C15C—N3B—C14B—N2B | −173.7 (10) |
C15A—N3A—C14A—N2A | 177.4 (3) | C11B—N2B—C14B—O2B | 173.9 (2) |
C12A—N2A—C14A—O2A | −9.0 (4) | C12B—N2B—C14B—O2B | 22.2 (3) |
C11A—N2A—C14A—O2A | −153.3 (3) | C11B—N2B—C14B—N3B | −10.5 (3) |
C12A—N2A—C14A—N3A | 174.1 (2) | C12B—N2B—C14B—N3B | −162.2 (2) |
C11A—N2A—C14A—N3A | 29.8 (3) | C14B—N3B—C15B—C16B | 162.7 (8) |
C14A—N3A—C15A—C16A | −128.1 (4) | C15C—N3B—C15B—C16B | 15 (3) |
C2B—O1B—C1B—C9B | 43.8 (3) | C14B—N3B—C15C—C16C | −106.6 (11) |
C2B—O1B—C1B—C10B | 164.34 (18) | C15B—N3B—C15C—C16C | −66 (4) |
C2B—O1B—C1B—C13B | −78.8 (2) |
Cg1 is the centroid of the C4B–C9B benzene ring |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H1N3···O2Ai | 0.81 (3) | 2.12 (3) | 2.915 (3) | 170 (3) |
N3B—H2N3···O2Bii | 0.83 (2) | 2.19 (3) | 2.983 (3) | 160 (2) |
C11A—H11B···O2Ai | 1.00 (3) | 2.27 (3) | 3.246 (3) | 165 (2) |
C11B—H11C···O2Bii | 0.95 (3) | 2.50 (3) | 3.344 (3) | 147 (2) |
C9B—H9B···O2Biii | 0.92 (3) | 2.58 (3) | 3.473 (3) | 163 (2) |
C13A—H13B···Cg1iv | 0.97 | 2.91 | 3.843 (3) | 163 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+2, −y+1, −z+2; (iv) x, −y−1/2, z−3/2. |
Experimental details
Crystal data | |
Chemical formula | C17H19N3O2 |
Mr | 297.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 22.7845 (8), 14.3370 (5), 9.8442 (3) |
β (°) | 90.783 (1) |
V (Å3) | 3215.42 (19) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker Kappa APEXII |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2008) |
Tmin, Tmax | 0.972, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26353, 5377, 3664 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.584 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.177, 1.04 |
No. of reflections | 5377 |
No. of parameters | 455 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.20 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLUTON (Spek, 2009).
Cg1 is the centroid of the C4B–C9B benzene ring |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H1N3···O2Ai | 0.81 (3) | 2.12 (3) | 2.915 (3) | 170 (3) |
N3B—H2N3···O2Bii | 0.83 (2) | 2.19 (3) | 2.983 (3) | 160 (2) |
C11A—H11B···O2Ai | 1.00 (3) | 2.27 (3) | 3.246 (3) | 165 (2) |
C11B—H11C···O2Bii | 0.95 (3) | 2.50 (3) | 3.344 (3) | 147 (2) |
C9B—H9B···O2Biii | 0.92 (3) | 2.58 (3) | 3.473 (3) | 163 (2) |
C13A—H13B···Cg1iv | 0.97 | 2.91 | 3.843 (3) | 163 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+2, −y+1, −z+2; (iv) x, −y−1/2, z−3/2. |
Acknowledgements
The authors thank the SAIF, IIT, Madras, India, for the
data collection facility.References
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Chromene with piperidine derivatives are potent agents inducing apoptosis (Kemnitzer et al., 2004). They also exhibit cytotoxic (Vosooghi et al., 2010), antifungal (Mahdavi et al., 2011) and antimycobacterial activities (Patil et al., 2012). In a continuation to our study of the structural features of 1'-benzyl spiro[chromene-2,4'-piperidine]-4-carbonitrile (Rajalakshmi et al., 2012), we report here the crystal structure of the title compound: 4-cyano-N-ethylspiro[chromene-2,4'-piperidine]- 1'-carboxamide.
The title compound contains two molecules in the asymmetric unit (Fig. 1). The piperidine ring forms dihedral angles of 11.9 (2)° and 78.2 (1)° for molecule A, 7.9 (8)° and 74.3 (1)° for molecule B, with the N-ethyl carboxamide group and chroman ring, respectively. The pyran ring in the molecules A and B (C8/C7/C2/O1/C1/C9) adopts a twisted conformation (5S4) with O1 and C1 atoms deviating respectively from the mean plane defined by the rest of the atoms by -0.1926 (5) Å and 0.2626 (5) Å in molecule A, and by -0.2375 (4) Å and 0.3063 (5) Å in molecule B. The piperidine ring (C1/C10/C11/N2/C12/C13) adopts a chair conformation (1C4) with C1 and N2 atoms deviating respectively from the rest of the atoms by -0.6644 (3) Å and 0.6065 (3) Å in molecule A and by -0.6418 (4) Å and 0.6263 (4)Å in molecule B (Cremer & Pople, 1975). In molecule B, the terminal ethyl group is disordered over two positions with refined occupancy ratios of 0.55 (1):0.45 (1).
Molecules A and B form separate chains along [001] through similar R21(7) motifs (Bernstein et al., 1995) through N—H···O and C—H···O hydrogen bonds. The chains made of molecules B form layers parallel to bc plane owing to formation of an additional C9B—H9B···O2B hydrogen bond. The crystal structure also has a noteworthy C—H···π interaction that appears to be a weaker link between molecules A and B resulting in layers parallel to the (100) plane (Fig.2 and Fig.3).