organic compounds
5′′-Benzylidene-5-chloro-1′,1′′-dimethyl-4′-phenyldispiro[indoline-3,2′-pyrrolidine-3′,3′′-piperidine]-2,4′′-dione
aSolid State Department, Physics Division, National Research Centre, Dokki, Giza, Egypt, bPesticide Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt, cPhysics Department, Faculty of Science, Helwan University, Helwan, Cairo, Egypt, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
The title compound, C30H28ClN3O2, features two spiro links, one connecting the piperidine and pyrrolidine rings, and the other connecting the pyrrolidine ring and indole residue. The configuration about the ethene bond is E. The piperidine ring adopts a half-chair conformation where the C atom connected to the spiro-C atom lies 0.713 (3) Å out of the plane of the remaining five atoms (r.m.s. deviation = 0.086 Å). The pyrrolidine ring has an with the flap atom being the methylene C atom. Centrosymmetric eight-membered {⋯HNCO}2 amide synthons feature in the crystal packing. These are consolidated into a three-dimensional architecture by phenyl–pyrrolidine C—H⋯N and chlorobenzene–pyrrolidine-bound phenyl C—H⋯π interactions.
CCDC reference: 917323
Related literature
For the biological activity of related spiropyrrolidine analogues, see: Girgis et al. (2012); Kumar et al. (2008). For related structural studies, see: Moustafa et al. (2012). For the synthesis of the precursor molecule, see: Al-Omary et al. (2012).
Experimental
Crystal data
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Data collection: COLLECT (Hooft, 1998); cell DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 917323
https://doi.org/10.1107/S1600536813032765/hg5367sup1.cif
contains datablocks general, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032765/hg5367Isup2.hkl
A mixture of equimolar amounts of 3E,5E-1-methyl-3,5-bis(phenylmethylidene)-4-piperidone (5 mmol), prepared by a literature procedure (Al-Omary et al., 2012), 5-chloroisatin and sarcosine in absolute ethanol (25 ml) was boiled under reflux (TLC monitoring). The separated solid was collected and crystallized from n-butanol affording (I). Reaction time 9 h. Colourless crystals. M.pt: 512–514 K. Yield 88%. Anal. Calcd. for C30H28ClN3O2 (498.03): C, 72.35; H, 5.67; N, 8.44. Found: C, 72.56; H, 5.81; N, 8.67. IR: νmax/cm-1: 3168 (N—H); 1688 (C═O); 1597, 1457 (C═C).
The C-bound H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The N-bound H-atoms were treated similarly with N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(N).
In connection with on-going studies of spiropyrrolidine derivatives (Girgis et al. 2012; Moustafa et al. 2012), the title compound, (I), was synthesised and characterised crystallographically. These compounds have biological activity and the structure of the skeltal structure is well established (Kumar et al. 2008).
There are two spiro links in the molecule, Fig. 1, i) where the piperidine and pyrrolidine rings are connected at C1, and ii) where the pyrrolidine ring and indole residue are connected at C6. The phenylmethylidene ═C11 double bond is E. The sum of the angles around the piperidine-N1 atom is approximately 333° confirming its sp3 character. The piperidine ring adopts a half-chair conformation where the C2 atom lies 0.713 (3) Å out of the plane of the remaining five atoms (r.m.s. deviation = 0.086 Å). The C6 and C8 atoms occupy axial and equatorial positions with respect to the piperidine ring, the phenylmethylidene residue occupies an equatorial position, and the N-bound methyl substituent is equatorial. The pyrrolidine ring has an with the flap atom being the C7 atom which lies 0.648 (3) Å out of the plane of the remaining four atoms (r.m.s. deviation = 0.026 Å). Finally, the indole fused ring system is planar with a r.m.s. deviation = 0.051 Å.
is connected to the piperidine ring at position C4 while the pyrrolidine-bound aryl ring is attached at C8. The conformation about the C4The most prominent feature of the crystal packing of is the formation of centrosymmetric eight-membered {···HNCO}2 synthons owing to the self-association of molecules via hydrogen bonding between amide groups, Table 1. The dimers are connected into a supramolecular chain parallel to the b axis by phenyl-C–H···N (pyrrolidine) interactions and these are consolidated into a three-dimensional architecture by (chlorobenzene)C—H···π (pyrrolidine-bound phenyl), edge-to-face, interactions; a view of the contents is shown in Fig. 2.
In connection with on-going studies of spiropyrrolidine derivatives (Girgis et al. 2012; Moustafa et al. 2012), the title compound, (I), was synthesised and characterised crystallographically. These compounds have biological activity and the structure of the skeltal structure is well established (Kumar et al. 2008).
There are two spiro links in the molecule, Fig. 1, i) where the piperidine and pyrrolidine rings are connected at C1, and ii) where the pyrrolidine ring and indole residue are connected at C6. The phenylmethylidene ═C11 double bond is E. The sum of the angles around the piperidine-N1 atom is approximately 333° confirming its sp3 character. The piperidine ring adopts a half-chair conformation where the C2 atom lies 0.713 (3) Å out of the plane of the remaining five atoms (r.m.s. deviation = 0.086 Å). The C6 and C8 atoms occupy axial and equatorial positions with respect to the piperidine ring, the phenylmethylidene residue occupies an equatorial position, and the N-bound methyl substituent is equatorial. The pyrrolidine ring has an with the flap atom being the C7 atom which lies 0.648 (3) Å out of the plane of the remaining four atoms (r.m.s. deviation = 0.026 Å). Finally, the indole fused ring system is planar with a r.m.s. deviation = 0.051 Å.
is connected to the piperidine ring at position C4 while the pyrrolidine-bound aryl ring is attached at C8. The conformation about the C4The most prominent feature of the crystal packing of is the formation of centrosymmetric eight-membered {···HNCO}2 synthons owing to the self-association of molecules via hydrogen bonding between amide groups, Table 1. The dimers are connected into a supramolecular chain parallel to the b axis by phenyl-C–H···N (pyrrolidine) interactions and these are consolidated into a three-dimensional architecture by (chlorobenzene)C—H···π (pyrrolidine-bound phenyl), edge-to-face, interactions; a view of the contents is shown in Fig. 2.
For the biological activity of related spiropyrrolidine analogues, see: Girgis et al. (2012); Kumar et al. (2008). For related structural studies, see: Moustafa et al. (2012). For the synthesis of the precursor molecule, see: Al-Omary et al. (2012).
A mixture of equimolar amounts of 3E,5E-1-methyl-3,5-bis(phenylmethylidene)-4-piperidone (5 mmol), prepared by a literature procedure (Al-Omary et al., 2012), 5-chloroisatin and sarcosine in absolute ethanol (25 ml) was boiled under reflux (TLC monitoring). The separated solid was collected and crystallized from n-butanol affording (I). Reaction time 9 h. Colourless crystals. M.pt: 512–514 K. Yield 88%. Anal. Calcd. for C30H28ClN3O2 (498.03): C, 72.35; H, 5.67; N, 8.44. Found: C, 72.56; H, 5.81; N, 8.67. IR: νmax/cm-1: 3168 (N—H); 1688 (C═O); 1597, 1457 (C═C).
detailsThe C-bound H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The N-bound H-atoms were treated similarly with N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(N).
Data collection: COLLECT (Hooft, 1998); cell
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. | |
Fig. 2. A view in projection down the c axis of the unit-cell contents for (I). The N—H···O, C—H···N and C—H···π interactions are shown as orange, blue and purple dashed lines, respectively. |
C30H28ClN3O2 | F(000) = 1048 |
Mr = 498.00 | Dx = 1.291 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5029 reflections |
a = 10.5028 (3) Å | θ = 2.9–27.5° |
b = 20.4117 (6) Å | µ = 0.18 mm−1 |
c = 11.9951 (4) Å | T = 293 K |
β = 94.877 (1)° | Block, colourless |
V = 2562.20 (14) Å3 | 0.52 × 0.22 × 0.15 mm |
Z = 4 |
Nonius 590 KappaCCD diffractometer | 2547 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
φ and ω scans | h = −13→13 |
10395 measured reflections | k = −24→26 |
5842 independent reflections | l = −15→15 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0569P)2] where P = (Fo2 + 2Fc2)/3 |
5842 reflections | (Δ/σ)max = 0.001 |
327 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C30H28ClN3O2 | V = 2562.20 (14) Å3 |
Mr = 498.00 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.5028 (3) Å | µ = 0.18 mm−1 |
b = 20.4117 (6) Å | T = 293 K |
c = 11.9951 (4) Å | 0.52 × 0.22 × 0.15 mm |
β = 94.877 (1)° |
Nonius 590 KappaCCD diffractometer | 2547 reflections with I > 2σ(I) |
10395 measured reflections | Rint = 0.066 |
5842 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.18 e Å−3 |
5842 reflections | Δρmin = −0.35 e Å−3 |
327 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
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 | 1.05716 (7) | 0.16826 (4) | −0.06845 (7) | 0.0777 (3) | |
O1 | 0.70008 (15) | 0.22207 (8) | 0.17686 (15) | 0.0518 (5) | |
O2 | 0.83631 (15) | 0.01572 (8) | 0.45243 (14) | 0.0501 (5) | |
N1 | 0.87248 (16) | 0.16478 (9) | 0.47693 (16) | 0.0395 (5) | |
N2 | 0.73065 (16) | 0.03868 (9) | 0.21124 (16) | 0.0425 (5) | |
N3 | 1.01454 (17) | 0.04625 (9) | 0.36752 (17) | 0.0441 (5) | |
H3n | 1.0711 | 0.0286 | 0.4142 | 0.053* | |
C1 | 0.72419 (19) | 0.13839 (11) | 0.31799 (19) | 0.0354 (6) | |
C2 | 0.7398 (2) | 0.14837 (11) | 0.44474 (19) | 0.0389 (6) | |
H2A | 0.6845 | 0.1835 | 0.4659 | 0.047* | |
H2B | 0.7165 | 0.1086 | 0.4825 | 0.047* | |
C3 | 0.8953 (2) | 0.23259 (11) | 0.4469 (2) | 0.0425 (6) | |
H3A | 0.9855 | 0.2423 | 0.4618 | 0.051* | |
H3B | 0.8485 | 0.2612 | 0.4935 | 0.051* | |
C4 | 0.8552 (2) | 0.24660 (11) | 0.32605 (19) | 0.0370 (6) | |
C5 | 0.7557 (2) | 0.20414 (11) | 0.2654 (2) | 0.0377 (6) | |
C6 | 0.81725 (19) | 0.08258 (11) | 0.27869 (19) | 0.0364 (6) | |
C7 | 0.6081 (2) | 0.04033 (11) | 0.2593 (2) | 0.0463 (7) | |
H7A | 0.6121 | 0.0177 | 0.3307 | 0.056* | |
H7B | 0.5409 | 0.0212 | 0.2091 | 0.056* | |
C8 | 0.58871 (19) | 0.11328 (11) | 0.2732 (2) | 0.0391 (6) | |
H8 | 0.5710 | 0.1315 | 0.1979 | 0.047* | |
C9 | 0.9106 (2) | 0.15392 (13) | 0.5956 (2) | 0.0562 (7) | |
H9A | 0.8554 | 0.1784 | 0.6401 | 0.084* | |
H9B | 0.9972 | 0.1681 | 0.6124 | 0.084* | |
H9C | 0.9041 | 0.1081 | 0.6124 | 0.084* | |
C10 | 0.7805 (2) | −0.02622 (13) | 0.1881 (2) | 0.0615 (8) | |
H10A | 0.8615 | −0.0219 | 0.1573 | 0.092* | |
H10B | 0.7216 | −0.0485 | 0.1354 | 0.092* | |
H10C | 0.7911 | −0.0510 | 0.2562 | 0.092* | |
C11 | 0.9050 (2) | 0.29475 (11) | 0.2683 (2) | 0.0423 (6) | |
H11 | 0.8740 | 0.2975 | 0.1935 | 0.051* | |
C12 | 1.0017 (2) | 0.34419 (11) | 0.3053 (2) | 0.0408 (6) | |
C13 | 1.0215 (2) | 0.36746 (13) | 0.4136 (2) | 0.0546 (7) | |
H13 | 0.9709 | 0.3519 | 0.4678 | 0.066* | |
C14 | 1.1149 (3) | 0.41337 (14) | 0.4432 (3) | 0.0657 (8) | |
H14 | 1.1273 | 0.4279 | 0.5168 | 0.079* | |
C15 | 1.1892 (3) | 0.43743 (14) | 0.3646 (3) | 0.0658 (8) | |
H15 | 1.2537 | 0.4674 | 0.3849 | 0.079* | |
C16 | 1.1685 (3) | 0.41725 (14) | 0.2555 (3) | 0.0667 (9) | |
H16 | 1.2169 | 0.4347 | 0.2012 | 0.080* | |
C17 | 1.0760 (2) | 0.37125 (12) | 0.2266 (2) | 0.0540 (7) | |
H17 | 1.0627 | 0.3579 | 0.1524 | 0.065* | |
C18 | 0.8882 (2) | 0.04577 (11) | 0.3795 (2) | 0.0407 (6) | |
C19 | 1.0428 (2) | 0.07885 (11) | 0.2700 (2) | 0.0385 (6) | |
C20 | 1.1587 (2) | 0.08588 (12) | 0.2266 (2) | 0.0485 (7) | |
H20 | 1.2336 | 0.0717 | 0.2662 | 0.058* | |
C21 | 1.1613 (2) | 0.11466 (12) | 0.1225 (2) | 0.0524 (7) | |
H21 | 1.2388 | 0.1201 | 0.0915 | 0.063* | |
C22 | 1.0499 (2) | 0.13532 (12) | 0.0645 (2) | 0.0478 (7) | |
C23 | 0.9324 (2) | 0.12955 (11) | 0.1090 (2) | 0.0435 (6) | |
H23 | 0.8577 | 0.1440 | 0.0693 | 0.052* | |
C24 | 0.9298 (2) | 0.10180 (11) | 0.2136 (2) | 0.0368 (6) | |
C25 | 0.4792 (2) | 0.13400 (12) | 0.3399 (2) | 0.0394 (6) | |
C26 | 0.4383 (2) | 0.09737 (14) | 0.4274 (2) | 0.0544 (7) | |
H26 | 0.4793 | 0.0582 | 0.4477 | 0.065* | |
C27 | 0.3363 (2) | 0.11858 (17) | 0.4853 (2) | 0.0652 (8) | |
H27 | 0.3094 | 0.0935 | 0.5436 | 0.078* | |
C28 | 0.2756 (3) | 0.17634 (18) | 0.4566 (3) | 0.0722 (9) | |
H28 | 0.2083 | 0.1907 | 0.4959 | 0.087* | |
C29 | 0.3145 (3) | 0.21279 (15) | 0.3698 (3) | 0.0701 (9) | |
H29 | 0.2731 | 0.2518 | 0.3497 | 0.084* | |
C30 | 0.4153 (2) | 0.19161 (13) | 0.3119 (2) | 0.0553 (7) | |
H30 | 0.4406 | 0.2167 | 0.2529 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0823 (5) | 0.0892 (6) | 0.0655 (6) | 0.0142 (4) | 0.0285 (4) | 0.0289 (4) |
O1 | 0.0515 (10) | 0.0547 (11) | 0.0467 (12) | −0.0077 (8) | −0.0102 (9) | 0.0147 (9) |
O2 | 0.0486 (10) | 0.0543 (11) | 0.0466 (12) | −0.0018 (9) | −0.0003 (9) | 0.0159 (9) |
N1 | 0.0364 (11) | 0.0465 (13) | 0.0341 (13) | −0.0047 (9) | −0.0047 (9) | 0.0055 (10) |
N2 | 0.0362 (11) | 0.0430 (13) | 0.0475 (14) | −0.0005 (10) | −0.0004 (10) | −0.0057 (10) |
N3 | 0.0350 (11) | 0.0538 (14) | 0.0420 (14) | 0.0067 (10) | −0.0051 (10) | 0.0087 (10) |
C1 | 0.0314 (12) | 0.0416 (15) | 0.0326 (15) | −0.0011 (11) | −0.0019 (10) | 0.0045 (12) |
C2 | 0.0385 (13) | 0.0408 (15) | 0.0369 (16) | −0.0052 (11) | 0.0010 (11) | 0.0029 (12) |
C3 | 0.0380 (13) | 0.0440 (16) | 0.0445 (17) | −0.0070 (11) | −0.0019 (11) | 0.0012 (13) |
C4 | 0.0345 (13) | 0.0433 (15) | 0.0328 (15) | −0.0015 (11) | 0.0004 (11) | 0.0029 (12) |
C5 | 0.0338 (13) | 0.0426 (15) | 0.0365 (17) | 0.0044 (11) | 0.0027 (12) | 0.0039 (13) |
C6 | 0.0344 (12) | 0.0389 (14) | 0.0349 (15) | −0.0007 (11) | −0.0032 (11) | 0.0030 (11) |
C7 | 0.0381 (14) | 0.0516 (17) | 0.0479 (17) | −0.0072 (12) | −0.0034 (12) | −0.0004 (13) |
C8 | 0.0333 (12) | 0.0450 (16) | 0.0378 (15) | −0.0002 (11) | −0.0033 (11) | 0.0037 (12) |
C9 | 0.0597 (16) | 0.0632 (19) | 0.0434 (19) | −0.0088 (14) | −0.0096 (13) | 0.0069 (14) |
C10 | 0.0593 (17) | 0.0547 (19) | 0.070 (2) | −0.0006 (14) | 0.0051 (15) | −0.0124 (15) |
C11 | 0.0415 (14) | 0.0472 (16) | 0.0379 (16) | 0.0002 (13) | 0.0014 (12) | −0.0011 (13) |
C12 | 0.0403 (13) | 0.0411 (15) | 0.0405 (17) | −0.0034 (12) | 0.0010 (12) | 0.0031 (13) |
C13 | 0.0698 (18) | 0.0511 (17) | 0.0429 (19) | −0.0159 (15) | 0.0052 (14) | 0.0042 (14) |
C14 | 0.085 (2) | 0.060 (2) | 0.049 (2) | −0.0203 (17) | −0.0112 (16) | 0.0024 (16) |
C15 | 0.0552 (18) | 0.060 (2) | 0.080 (3) | −0.0204 (14) | −0.0069 (17) | 0.0028 (18) |
C16 | 0.0612 (18) | 0.066 (2) | 0.076 (3) | −0.0189 (16) | 0.0223 (17) | −0.0040 (18) |
C17 | 0.0590 (16) | 0.0555 (17) | 0.0490 (19) | −0.0108 (15) | 0.0136 (14) | −0.0047 (15) |
C18 | 0.0404 (15) | 0.0385 (15) | 0.0424 (17) | 0.0005 (12) | −0.0014 (12) | 0.0041 (13) |
C19 | 0.0393 (14) | 0.0391 (15) | 0.0363 (16) | 0.0001 (11) | −0.0004 (12) | −0.0020 (12) |
C20 | 0.0363 (14) | 0.0548 (17) | 0.0537 (19) | 0.0049 (12) | 0.0003 (13) | −0.0009 (14) |
C21 | 0.0422 (15) | 0.0568 (18) | 0.060 (2) | −0.0043 (13) | 0.0140 (14) | −0.0018 (15) |
C22 | 0.0522 (16) | 0.0494 (17) | 0.0430 (18) | 0.0022 (13) | 0.0120 (14) | 0.0046 (13) |
C23 | 0.0407 (14) | 0.0439 (16) | 0.0450 (17) | 0.0038 (12) | −0.0009 (12) | 0.0048 (13) |
C24 | 0.0375 (13) | 0.0371 (14) | 0.0354 (16) | 0.0005 (11) | 0.0001 (11) | −0.0005 (12) |
C25 | 0.0291 (12) | 0.0450 (16) | 0.0430 (17) | −0.0059 (12) | −0.0040 (11) | −0.0003 (13) |
C26 | 0.0436 (15) | 0.0665 (19) | 0.0527 (19) | −0.0041 (14) | 0.0013 (14) | 0.0088 (15) |
C27 | 0.0514 (17) | 0.095 (3) | 0.050 (2) | −0.0111 (17) | 0.0109 (15) | −0.0051 (17) |
C28 | 0.0448 (17) | 0.096 (3) | 0.077 (3) | −0.0018 (18) | 0.0135 (16) | −0.030 (2) |
C29 | 0.0516 (18) | 0.063 (2) | 0.097 (3) | 0.0026 (15) | 0.0102 (18) | −0.0110 (19) |
C30 | 0.0409 (15) | 0.0537 (18) | 0.071 (2) | −0.0044 (14) | 0.0042 (14) | −0.0004 (15) |
Cl1—C22 | 1.738 (3) | C10—H10C | 0.9600 |
O1—C5 | 1.224 (3) | C11—C12 | 1.473 (3) |
O2—C18 | 1.232 (3) | C11—H11 | 0.9300 |
N1—C2 | 1.453 (3) | C12—C13 | 1.382 (3) |
N1—C3 | 1.455 (3) | C12—C17 | 1.390 (3) |
N1—C9 | 1.463 (3) | C13—C14 | 1.381 (4) |
N2—C7 | 1.454 (3) | C13—H13 | 0.9300 |
N2—C10 | 1.460 (3) | C14—C15 | 1.366 (4) |
N2—C6 | 1.470 (3) | C14—H14 | 0.9300 |
N3—C18 | 1.347 (3) | C15—C16 | 1.371 (4) |
N3—C19 | 1.400 (3) | C15—H15 | 0.9300 |
N3—H3n | 0.8600 | C16—C17 | 1.374 (3) |
C1—C5 | 1.531 (3) | C16—H16 | 0.9300 |
C1—C2 | 1.529 (3) | C17—H17 | 0.9300 |
C1—C8 | 1.564 (3) | C19—C20 | 1.371 (3) |
C1—C6 | 1.598 (3) | C19—C24 | 1.396 (3) |
C2—H2A | 0.9700 | C20—C21 | 1.382 (3) |
C2—H2B | 0.9700 | C20—H20 | 0.9300 |
C3—C4 | 1.502 (3) | C21—C22 | 1.375 (3) |
C3—H3A | 0.9700 | C21—H21 | 0.9300 |
C3—H3B | 0.9700 | C22—C23 | 1.391 (3) |
C4—C11 | 1.334 (3) | C23—C24 | 1.380 (3) |
C4—C5 | 1.498 (3) | C23—H23 | 0.9300 |
C6—C24 | 1.522 (3) | C25—C30 | 1.381 (3) |
C6—C18 | 1.559 (3) | C25—C26 | 1.386 (3) |
C7—C8 | 1.514 (3) | C26—C27 | 1.394 (3) |
C7—H7A | 0.9700 | C26—H26 | 0.9300 |
C7—H7B | 0.9700 | C27—C28 | 1.370 (4) |
C8—C25 | 1.516 (3) | C27—H27 | 0.9300 |
C8—H8 | 0.9800 | C28—C29 | 1.370 (4) |
C9—H9A | 0.9600 | C28—H28 | 0.9300 |
C9—H9B | 0.9600 | C29—C30 | 1.384 (4) |
C9—H9C | 0.9600 | C29—H29 | 0.9300 |
C10—H10A | 0.9600 | C30—H30 | 0.9300 |
C10—H10B | 0.9600 | ||
C2—N1—C3 | 109.14 (18) | H10B—C10—H10C | 109.5 |
C2—N1—C9 | 113.61 (17) | C4—C11—C12 | 129.7 (2) |
C3—N1—C9 | 110.35 (18) | C4—C11—H11 | 115.2 |
C7—N2—C10 | 116.12 (18) | C12—C11—H11 | 115.2 |
C7—N2—C6 | 107.14 (17) | C13—C12—C17 | 117.0 (2) |
C10—N2—C6 | 116.30 (18) | C13—C12—C11 | 124.3 (2) |
C18—N3—C19 | 111.96 (19) | C17—C12—C11 | 118.7 (2) |
C18—N3—H3n | 124.0 | C14—C13—C12 | 121.5 (2) |
C19—N3—H3n | 124.0 | C14—C13—H13 | 119.3 |
C5—C1—C2 | 106.50 (19) | C12—C13—H13 | 119.3 |
C5—C1—C8 | 111.60 (18) | C15—C14—C13 | 120.1 (3) |
C2—C1—C8 | 113.73 (17) | C15—C14—H14 | 120.0 |
C5—C1—C6 | 110.15 (16) | C13—C14—H14 | 120.0 |
C2—C1—C6 | 111.83 (18) | C14—C15—C16 | 119.8 (3) |
C8—C1—C6 | 103.10 (17) | C14—C15—H15 | 120.1 |
N1—C2—C1 | 108.31 (17) | C16—C15—H15 | 120.1 |
N1—C2—H2A | 110.0 | C15—C16—C17 | 119.9 (3) |
C1—C2—H2A | 110.0 | C15—C16—H16 | 120.1 |
N1—C2—H2B | 110.0 | C17—C16—H16 | 120.1 |
C1—C2—H2B | 110.0 | C16—C17—C12 | 121.7 (3) |
H2A—C2—H2B | 108.4 | C16—C17—H17 | 119.2 |
N1—C3—C4 | 112.41 (19) | C12—C17—H17 | 119.2 |
N1—C3—H3A | 109.1 | O2—C18—N3 | 125.4 (2) |
C4—C3—H3A | 109.1 | O2—C18—C6 | 125.4 (2) |
N1—C3—H3B | 109.1 | N3—C18—C6 | 108.9 (2) |
C4—C3—H3B | 109.1 | C20—C19—C24 | 121.8 (2) |
H3A—C3—H3B | 107.9 | C20—C19—N3 | 128.7 (2) |
C11—C4—C5 | 117.5 (2) | C24—C19—N3 | 109.40 (19) |
C11—C4—C3 | 123.4 (2) | C19—C20—C21 | 118.2 (2) |
C5—C4—C3 | 119.0 (2) | C19—C20—H20 | 120.9 |
O1—C5—C4 | 120.7 (2) | C21—C20—H20 | 120.9 |
O1—C5—C1 | 121.0 (2) | C22—C21—C20 | 120.4 (2) |
C4—C5—C1 | 118.3 (2) | C22—C21—H21 | 119.8 |
N2—C6—C24 | 110.25 (18) | C20—C21—H21 | 119.8 |
N2—C6—C18 | 111.47 (18) | C21—C22—C23 | 121.6 (2) |
C24—C6—C18 | 100.44 (17) | C21—C22—Cl1 | 118.77 (19) |
N2—C6—C1 | 103.40 (16) | C23—C22—Cl1 | 119.6 (2) |
C24—C6—C1 | 119.26 (18) | C24—C23—C22 | 118.1 (2) |
C18—C6—C1 | 112.25 (18) | C24—C23—H23 | 121.0 |
N2—C7—C8 | 101.46 (17) | C22—C23—H23 | 121.0 |
N2—C7—H7A | 111.5 | C23—C24—C19 | 119.8 (2) |
C8—C7—H7A | 111.5 | C23—C24—C6 | 130.4 (2) |
N2—C7—H7B | 111.5 | C19—C24—C6 | 109.3 (2) |
C8—C7—H7B | 111.5 | C30—C25—C26 | 117.9 (2) |
H7A—C7—H7B | 109.3 | C30—C25—C8 | 118.9 (2) |
C7—C8—C25 | 116.62 (19) | C26—C25—C8 | 123.2 (2) |
C7—C8—C1 | 103.47 (17) | C25—C26—C27 | 120.7 (3) |
C25—C8—C1 | 115.89 (19) | C25—C26—H26 | 119.7 |
C7—C8—H8 | 106.7 | C27—C26—H26 | 119.7 |
C25—C8—H8 | 106.7 | C28—C27—C26 | 120.2 (3) |
C1—C8—H8 | 106.7 | C28—C27—H27 | 119.9 |
N1—C9—H9A | 109.5 | C26—C27—H27 | 119.9 |
N1—C9—H9B | 109.5 | C29—C28—C27 | 119.7 (3) |
H9A—C9—H9B | 109.5 | C29—C28—H28 | 120.1 |
N1—C9—H9C | 109.5 | C27—C28—H28 | 120.1 |
H9A—C9—H9C | 109.5 | C28—C29—C30 | 120.1 (3) |
H9B—C9—H9C | 109.5 | C28—C29—H29 | 119.9 |
N2—C10—H10A | 109.5 | C30—C29—H29 | 119.9 |
N2—C10—H10B | 109.5 | C25—C30—C29 | 121.4 (3) |
H10A—C10—H10B | 109.5 | C25—C30—H30 | 119.3 |
N2—C10—H10C | 109.5 | C29—C30—H30 | 119.3 |
H10A—C10—H10C | 109.5 | ||
C3—N1—C2—C1 | 76.1 (2) | C11—C12—C13—C14 | 179.2 (2) |
C9—N1—C2—C1 | −160.35 (19) | C12—C13—C14—C15 | 0.8 (4) |
C5—C1—C2—N1 | −62.7 (2) | C13—C14—C15—C16 | 1.8 (4) |
C8—C1—C2—N1 | 173.98 (18) | C14—C15—C16—C17 | −2.2 (4) |
C6—C1—C2—N1 | 57.7 (2) | C15—C16—C17—C12 | 0.0 (4) |
C2—N1—C3—C4 | −53.4 (2) | C13—C12—C17—C16 | 2.4 (4) |
C9—N1—C3—C4 | −178.89 (18) | C11—C12—C17—C16 | −179.5 (2) |
N1—C3—C4—C11 | −155.0 (2) | C19—N3—C18—O2 | 173.4 (2) |
N1—C3—C4—C5 | 24.1 (3) | C19—N3—C18—C6 | −0.1 (3) |
C11—C4—C5—O1 | −17.4 (3) | N2—C6—C18—O2 | −56.8 (3) |
C3—C4—C5—O1 | 163.4 (2) | C24—C6—C18—O2 | −173.6 (2) |
C11—C4—C5—C1 | 163.4 (2) | C1—C6—C18—O2 | 58.7 (3) |
C3—C4—C5—C1 | −15.7 (3) | N2—C6—C18—N3 | 116.7 (2) |
C2—C1—C5—O1 | −145.8 (2) | C24—C6—C18—N3 | 0.0 (2) |
C8—C1—C5—O1 | −21.2 (3) | C1—C6—C18—N3 | −127.80 (19) |
C6—C1—C5—O1 | 92.7 (2) | C18—N3—C19—C20 | −175.8 (2) |
C2—C1—C5—C4 | 33.3 (2) | C18—N3—C19—C24 | 0.3 (3) |
C8—C1—C5—C4 | 157.97 (19) | C24—C19—C20—C21 | −2.2 (4) |
C6—C1—C5—C4 | −88.1 (2) | N3—C19—C20—C21 | 173.5 (2) |
C7—N2—C6—C24 | −160.87 (19) | C19—C20—C21—C22 | −0.2 (4) |
C10—N2—C6—C24 | 67.3 (3) | C20—C21—C22—C23 | 1.6 (4) |
C7—N2—C6—C18 | 88.5 (2) | C20—C21—C22—Cl1 | −177.5 (2) |
C10—N2—C6—C18 | −43.3 (3) | C21—C22—C23—C24 | −0.5 (4) |
C7—N2—C6—C1 | −32.3 (2) | Cl1—C22—C23—C24 | 178.52 (19) |
C10—N2—C6—C1 | −164.09 (19) | C22—C23—C24—C19 | −1.8 (3) |
C5—C1—C6—N2 | −114.14 (19) | C22—C23—C24—C6 | −173.0 (2) |
C2—C1—C6—N2 | 127.64 (18) | C20—C19—C24—C23 | 3.2 (3) |
C8—C1—C6—N2 | 5.1 (2) | N3—C19—C24—C23 | −173.2 (2) |
C5—C1—C6—C24 | 8.6 (3) | C20—C19—C24—C6 | 176.1 (2) |
C2—C1—C6—C24 | −109.6 (2) | N3—C19—C24—C6 | −0.3 (3) |
C8—C1—C6—C24 | 127.8 (2) | N2—C6—C24—C23 | 54.4 (3) |
C5—C1—C6—C18 | 125.6 (2) | C18—C6—C24—C23 | 172.1 (2) |
C2—C1—C6—C18 | 7.4 (2) | C1—C6—C24—C23 | −64.9 (3) |
C8—C1—C6—C18 | −115.19 (19) | N2—C6—C24—C19 | −117.5 (2) |
C10—N2—C7—C8 | 179.1 (2) | C18—C6—C24—C19 | 0.2 (2) |
C6—N2—C7—C8 | 47.2 (2) | C1—C6—C24—C19 | 123.2 (2) |
N2—C7—C8—C25 | −170.10 (19) | C7—C8—C25—C30 | −147.6 (2) |
N2—C7—C8—C1 | −41.6 (2) | C1—C8—C25—C30 | 90.2 (3) |
C5—C1—C8—C7 | 140.24 (19) | C7—C8—C25—C26 | 31.5 (3) |
C2—C1—C8—C7 | −99.2 (2) | C1—C8—C25—C26 | −90.7 (3) |
C6—C1—C8—C7 | 22.0 (2) | C30—C25—C26—C27 | −0.4 (4) |
C5—C1—C8—C25 | −90.8 (2) | C8—C25—C26—C27 | −179.5 (2) |
C2—C1—C8—C25 | 29.7 (3) | C25—C26—C27—C28 | −0.4 (4) |
C6—C1—C8—C25 | 150.97 (19) | C26—C27—C28—C29 | 0.8 (4) |
C5—C4—C11—C12 | 179.0 (2) | C27—C28—C29—C30 | −0.5 (4) |
C3—C4—C11—C12 | −1.9 (4) | C26—C25—C30—C29 | 0.7 (4) |
C4—C11—C12—C13 | −28.2 (4) | C8—C25—C30—C29 | 179.9 (2) |
C4—C11—C12—C17 | 153.9 (2) | C28—C29—C30—C25 | −0.3 (4) |
C17—C12—C13—C14 | −2.9 (4) |
Cg1 is the centroid of the C25–C30 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3n···O2i | 0.86 | 2.01 | 2.854 (3) | 165 |
C14—H14···N2ii | 0.93 | 2.58 | 3.480 (4) | 163 |
C20—H20···Cg1iii | 0.93 | 2.70 | 3.268 (3) | 121 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) x+1, y, z. |
Cg1 is the centroid of the C25–C30 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3n···O2i | 0.86 | 2.01 | 2.854 (3) | 165 |
C14—H14···N2ii | 0.93 | 2.58 | 3.480 (4) | 163 |
C20—H20···Cg1iii | 0.93 | 2.70 | 3.268 (3) | 121 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) x+1, y, z. |
Footnotes
‡Additional correspondence author, e-mail: ibfarag2002@yahoo.com.
Acknowledgements
This study was supported financially by the Science and Technology Development Fund (STDF), Egypt (grant No. 1133).
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