organic compounds
{1′-Phenyl-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tolyl)methanone
aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com
In the title compound, C35H29N3O, the quinoxaline and indene systems are essentially planar, with maximum deviations of 0.047 (2) and 0.032 (2) Å for C atoms, respectively. The quinoxaline system forms a dihedral angle of 4.75 (3)° with the indene system. The pyrrolizine system is folded. The substituted five-membered ring adopts an In the other five-membered ring, one C atom is disordered with a site-occupancy ratio of 0.676 (12):0.324 (12). In the crystal, molecules are linked via C—H⋯O hydrogen bonds involving the bifurcated carbonyl O atom.
Related literature
For the uses of pyrrolidine and quinoxaline derivatives, see: Amal Raj et al. (2003); Zarranz et al. (2003). For a related structure, see: Gayathri et al. (2005).;
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell APEX2; data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812031480/bt5959sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031480/bt5959Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812031480/bt5959Isup3.cml
A mixture of ninhydrin (1 mmol) and 1, 2-phenylenediamine (1 mmol) was stirred for 10 min in 10 mL of toluene followed by the addition of L-proline (1 mmol) and a solution of (E)-3-phenyl-1-p-tolylprop-2-en-1-one (1 mmol) in 10 ml of toluene. The mixture was then refluxed until completion of the reaction as evidenced by TLC. The solvent was removed in vacuo and the crude product was subjected to
using petroleum ether/ethyl acetate (4:1) as eluent.Hydrogen atoms were placed in calculated positions with C—H = 0.93 Å to 0.98 Å and refined using a riding model with fixed isotropic displacement parameters:Uiso(H) = 1.5Ueq(C) for methyl group and Uiso(H) = 1.2Ueq(C) for other groups. The distances between the disordered atoms and its neighbours were restrained to be equal with an effective e.s.d. of 0.01Å and the components of the ADP's of C25 and C26A in direction of the bond between them were restrained to be equal with an effective e.s.d. of 0.01Å2.
Pyrrolidine derivatives are found to have anticonvulsant, antimicrobial and antifungal activities against various pathogens (Amal Raj et al., 2003). Quinoxaline derivatives shown antibacterial, antiviral and anticancer properties (Zarranz et al., 2003). As spiro pyrrolidine compounds are of great medicinal properties, we have undertaken the three dimensional structure of the title compound.
X-ray analysis confirms the molecular structure and atom connectivity of the compound as illustrated in Fig. 1. The quinoxaline moiety is essentially planar with a maximum deviation of -0.0472 (23) Å for C21 atom, and it forms the dihedral angles of 4.75 (3), 54.94 (5) and 29.70 (6) ° with the indene moiety, phenyl rings (C2–C7) and (C30–C35), respectively. The indene moiety is also essentially planar with a maximum deviation of 0.0320 (16) Å for C18 atom, and it forms the dihedral angles of 51.75 (6) and 32.41 (6) ° with the phenyl rings (C2–C7) and (C30–C35), respectively.
The pyrrolizine moiety is folded and twisted about the N—C bond common to the two five membered rings. The indene fused with quinoxaline, subsituted five membered ring adopts twisted conformation on C9 and C29 atoms with the puckering parameters of Q2 = 0.3846 (17) Å, φ2 = 95.8 (3) °. The unsubsituted five-membered ring has a disordered C atom with occupancy factor of 0.676 (12)/0.324 (12). The five-membered ring (N1/C25/C26A/C27/C28) adopts an on C26A for major occupancy atom with the puckering parameters Q2 = 0.309 (4) Å, φ2 = 77.9 (5) °. The five-membered ring (N1/C25/C26B/C27/C28) adopts an on C26B for minor occupancy atom with the puckering parameters Q2 = 0.238 (6) Å, φ2 = 247.0 (10) °. The title compound exhibits structural similarities with the already reported related structures (Gayathri et al.2005).
In the crystal packing, molecules are linked via bifurcated C—H···O intermolecular hydrogen bonds involving the carbonyl group O atom as a single acceptor (Table. 1). The packing view of the compound is shown in Fig. 2.
For the uses of pyrrolidine and quinoxaline derivatives, see: Amal Raj et al. (2003); Zarranz et al. (2003). For a related structure, see: Gayathri et al. (2005).;
Data collection: APEX2 (Bruker, 2008); cell
APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C35H29N3O | F(000) = 2144 |
Mr = 507.61 | Dx = 1.246 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6643 reflections |
a = 16.4102 (6) Å | θ = 2.0–28.3° |
b = 16.4371 (6) Å | µ = 0.08 mm−1 |
c = 20.0648 (7) Å | T = 293 K |
V = 5412.2 (3) Å3 | Block, colourless |
Z = 8 | 0.35 × 0.30 × 0.25 mm |
Bruker SMART APEXII area-detector diffractometer | 3751 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 28.3°, θmin = 2.0° |
ω and φ scans | h = −18→21 |
47718 measured reflections | k = −21→21 |
6643 independent reflections | l = −25→26 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0614P)2 + 1.0312P] where P = (Fo2 + 2Fc2)/3 |
6643 reflections | (Δ/σ)max < 0.001 |
363 parameters | Δρmax = 0.26 e Å−3 |
3 restraints | Δρmin = −0.25 e Å−3 |
C35H29N3O | V = 5412.2 (3) Å3 |
Mr = 507.61 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 16.4102 (6) Å | µ = 0.08 mm−1 |
b = 16.4371 (6) Å | T = 293 K |
c = 20.0648 (7) Å | 0.35 × 0.30 × 0.25 mm |
Bruker SMART APEXII area-detector diffractometer | 3751 reflections with I > 2σ(I) |
47718 measured reflections | Rint = 0.044 |
6643 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 3 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.26 e Å−3 |
6643 reflections | Δρmin = −0.25 e Å−3 |
363 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. |
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 > 2sigma(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) | |
O1 | 0.10252 (8) | 0.10058 (8) | 0.72132 (6) | 0.0618 (4) | |
N1 | 0.01215 (8) | −0.11050 (9) | 0.82474 (7) | 0.0508 (4) | |
N2 | 0.17619 (9) | −0.11583 (8) | 0.89736 (7) | 0.0494 (4) | |
N3 | 0.15224 (9) | −0.00304 (10) | 1.00457 (7) | 0.0574 (4) | |
C1 | 0.44254 (11) | 0.18403 (13) | 0.86999 (10) | 0.0686 (6) | |
H1A | 0.4539 | 0.1586 | 0.9121 | 0.103* | |
H1B | 0.4368 | 0.2417 | 0.8762 | 0.103* | |
H1C | 0.4866 | 0.1736 | 0.8397 | 0.103* | |
C2 | 0.36464 (10) | 0.14989 (11) | 0.84176 (8) | 0.0506 (4) | |
C3 | 0.30762 (11) | 0.19957 (11) | 0.81147 (10) | 0.0619 (5) | |
H3 | 0.3171 | 0.2553 | 0.8094 | 0.074* | |
C4 | 0.23703 (12) | 0.16835 (11) | 0.78430 (10) | 0.0588 (5) | |
H4 | 0.2003 | 0.2032 | 0.7635 | 0.071* | |
C5 | 0.21991 (10) | 0.08581 (10) | 0.78749 (7) | 0.0432 (4) | |
C6 | 0.27605 (10) | 0.03572 (10) | 0.81850 (8) | 0.0481 (4) | |
H6 | 0.2658 | −0.0198 | 0.8217 | 0.058* | |
C7 | 0.34726 (10) | 0.06738 (11) | 0.84484 (9) | 0.0525 (4) | |
H7 | 0.3844 | 0.0325 | 0.8651 | 0.063* | |
C8 | 0.14256 (10) | 0.05584 (10) | 0.75697 (8) | 0.0445 (4) | |
C9 | 0.11326 (9) | −0.03001 (10) | 0.77066 (7) | 0.0413 (4) | |
H9 | 0.1610 | −0.0658 | 0.7723 | 0.050* | |
C10 | 0.06490 (10) | −0.03986 (10) | 0.83808 (7) | 0.0436 (4) | |
C11 | 0.02337 (10) | 0.03781 (10) | 0.86317 (8) | 0.0482 (4) | |
C12 | 0.05057 (11) | 0.05879 (10) | 0.92674 (8) | 0.0503 (4) | |
C13 | 0.02162 (13) | 0.12754 (12) | 0.95904 (10) | 0.0685 (6) | |
H13 | 0.0401 | 0.1411 | 1.0014 | 0.082* | |
C14 | −0.03536 (15) | 0.17546 (13) | 0.92672 (12) | 0.0805 (7) | |
H14 | −0.0553 | 0.2220 | 0.9474 | 0.097* | |
C15 | −0.06280 (14) | 0.15450 (14) | 0.86396 (12) | 0.0767 (6) | |
H15 | −0.1015 | 0.1870 | 0.8431 | 0.092* | |
C16 | −0.03374 (12) | 0.08618 (13) | 0.83169 (10) | 0.0636 (5) | |
H16 | −0.0524 | 0.0729 | 0.7893 | 0.076* | |
C17 | 0.11145 (10) | −0.00050 (10) | 0.94844 (8) | 0.0461 (4) | |
C18 | 0.12229 (10) | −0.05761 (10) | 0.89607 (7) | 0.0425 (4) | |
C19 | 0.22135 (10) | −0.11977 (10) | 0.95527 (9) | 0.0510 (4) | |
C20 | 0.20808 (11) | −0.06546 (11) | 1.00866 (8) | 0.0547 (4) | |
C21 | 0.25522 (14) | −0.07419 (14) | 1.06687 (10) | 0.0742 (6) | |
H21 | 0.2462 | −0.0398 | 1.1029 | 0.089* | |
C22 | 0.31366 (15) | −0.13228 (15) | 1.07069 (12) | 0.0835 (7) | |
H22 | 0.3440 | −0.1376 | 1.1096 | 0.100* | |
C23 | 0.32873 (14) | −0.18387 (14) | 1.01731 (12) | 0.0807 (7) | |
H23 | 0.3703 | −0.2222 | 1.0203 | 0.097* | |
C24 | 0.28306 (13) | −0.17897 (12) | 0.96040 (10) | 0.0687 (6) | |
H24 | 0.2927 | −0.2146 | 0.9253 | 0.082* | |
C25 | −0.07181 (12) | −0.11437 (16) | 0.84711 (11) | 0.0787 (7) | |
H25A | −0.0855 | −0.0668 | 0.8734 | 0.094* | 0.676 (12) |
H25B | −0.0809 | −0.1627 | 0.8739 | 0.094* | 0.676 (12) |
H25C | −0.0954 | −0.0603 | 0.8484 | 0.094* | 0.324 (12) |
H25D | −0.0747 | −0.1377 | 0.8915 | 0.094* | 0.324 (12) |
C26A | −0.1208 (2) | −0.1172 (5) | 0.7858 (2) | 0.0808 (16) | 0.676 (12) |
H26A | −0.1341 | −0.0626 | 0.7710 | 0.097* | 0.676 (12) |
H26B | −0.1712 | −0.1467 | 0.7934 | 0.097* | 0.676 (12) |
C26B | −0.1160 (5) | −0.1655 (8) | 0.7995 (4) | 0.065 (3) | 0.324 (12) |
H26C | −0.1713 | −0.1460 | 0.7939 | 0.078* | 0.324 (12) |
H26D | −0.1179 | −0.2214 | 0.8151 | 0.078* | 0.324 (12) |
C27 | −0.06970 (12) | −0.15994 (16) | 0.73483 (10) | 0.0744 (6) | |
H27A | −0.0827 | −0.1415 | 0.6901 | 0.089* | 0.676 (12) |
H27B | −0.0770 | −0.2184 | 0.7372 | 0.089* | 0.676 (12) |
H27C | −0.0938 | −0.1193 | 0.7059 | 0.089* | 0.324 (12) |
H27D | −0.0698 | −0.2119 | 0.7119 | 0.089* | 0.324 (12) |
C28 | 0.01680 (10) | −0.13568 (11) | 0.75445 (8) | 0.0510 (4) | |
H28 | 0.0528 | −0.1830 | 0.7505 | 0.061* | |
C29 | 0.05461 (10) | −0.06337 (10) | 0.71784 (7) | 0.0441 (4) | |
H29 | 0.0120 | −0.0228 | 0.7099 | 0.053* | |
C30 | 0.09388 (10) | −0.08434 (11) | 0.65201 (8) | 0.0471 (4) | |
C31 | 0.06495 (14) | −0.05272 (14) | 0.59322 (9) | 0.0743 (6) | |
H31 | 0.0208 | −0.0173 | 0.5941 | 0.089* | |
C32 | 0.09995 (17) | −0.07242 (17) | 0.53289 (10) | 0.0934 (8) | |
H32 | 0.0789 | −0.0504 | 0.4938 | 0.112* | |
C33 | 0.16483 (15) | −0.12356 (15) | 0.52992 (10) | 0.0794 (7) | |
H33 | 0.1885 | −0.1365 | 0.4891 | 0.095* | |
C34 | 0.19473 (13) | −0.15567 (14) | 0.58740 (10) | 0.0720 (6) | |
H34 | 0.2392 | −0.1908 | 0.5859 | 0.086* | |
C35 | 0.15961 (11) | −0.13657 (13) | 0.64785 (9) | 0.0601 (5) | |
H35 | 0.1806 | −0.1593 | 0.6866 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0607 (8) | 0.0626 (8) | 0.0621 (8) | 0.0001 (7) | −0.0130 (6) | 0.0174 (6) |
N1 | 0.0495 (8) | 0.0587 (9) | 0.0441 (8) | −0.0123 (7) | 0.0010 (6) | −0.0024 (6) |
N2 | 0.0563 (8) | 0.0482 (8) | 0.0436 (8) | 0.0015 (7) | −0.0056 (7) | 0.0016 (6) |
N3 | 0.0650 (9) | 0.0627 (9) | 0.0447 (8) | −0.0033 (8) | −0.0066 (7) | −0.0078 (7) |
C1 | 0.0559 (11) | 0.0729 (13) | 0.0769 (14) | −0.0180 (10) | −0.0028 (10) | −0.0010 (11) |
C2 | 0.0476 (10) | 0.0556 (10) | 0.0487 (10) | −0.0081 (9) | 0.0067 (8) | −0.0055 (8) |
C3 | 0.0587 (11) | 0.0429 (10) | 0.0840 (14) | −0.0057 (9) | −0.0002 (10) | −0.0009 (9) |
C4 | 0.0536 (11) | 0.0450 (10) | 0.0779 (13) | 0.0023 (9) | −0.0038 (9) | 0.0045 (9) |
C5 | 0.0443 (9) | 0.0432 (9) | 0.0419 (9) | −0.0002 (7) | 0.0024 (7) | −0.0004 (7) |
C6 | 0.0491 (9) | 0.0427 (9) | 0.0525 (10) | −0.0036 (8) | −0.0005 (8) | 0.0008 (7) |
C7 | 0.0470 (9) | 0.0557 (11) | 0.0550 (10) | −0.0004 (9) | −0.0040 (8) | 0.0035 (8) |
C8 | 0.0456 (9) | 0.0495 (9) | 0.0386 (8) | 0.0027 (8) | 0.0013 (7) | 0.0009 (7) |
C9 | 0.0404 (8) | 0.0464 (9) | 0.0372 (8) | −0.0006 (7) | −0.0028 (7) | −0.0019 (7) |
C10 | 0.0453 (9) | 0.0482 (9) | 0.0373 (8) | −0.0018 (8) | −0.0020 (7) | −0.0001 (7) |
C11 | 0.0463 (9) | 0.0534 (10) | 0.0449 (9) | 0.0019 (8) | 0.0030 (7) | 0.0026 (8) |
C12 | 0.0538 (10) | 0.0497 (10) | 0.0474 (10) | −0.0022 (8) | 0.0040 (8) | −0.0034 (8) |
C13 | 0.0794 (14) | 0.0608 (12) | 0.0653 (13) | 0.0071 (11) | 0.0020 (11) | −0.0152 (10) |
C14 | 0.0912 (16) | 0.0629 (13) | 0.0876 (16) | 0.0209 (12) | 0.0099 (13) | −0.0118 (12) |
C15 | 0.0751 (14) | 0.0733 (14) | 0.0817 (15) | 0.0268 (12) | 0.0058 (12) | 0.0067 (12) |
C16 | 0.0630 (12) | 0.0727 (13) | 0.0549 (11) | 0.0139 (10) | 0.0014 (9) | 0.0049 (10) |
C17 | 0.0507 (9) | 0.0486 (9) | 0.0389 (9) | −0.0062 (8) | −0.0010 (7) | −0.0017 (7) |
C18 | 0.0470 (9) | 0.0428 (9) | 0.0377 (8) | −0.0056 (8) | −0.0007 (7) | 0.0010 (7) |
C19 | 0.0546 (10) | 0.0519 (10) | 0.0466 (10) | −0.0043 (8) | −0.0071 (8) | 0.0070 (8) |
C20 | 0.0586 (11) | 0.0604 (11) | 0.0450 (10) | −0.0083 (9) | −0.0095 (8) | 0.0022 (8) |
C21 | 0.0857 (15) | 0.0818 (15) | 0.0552 (12) | −0.0032 (13) | −0.0243 (11) | −0.0026 (10) |
C22 | 0.0901 (16) | 0.0902 (17) | 0.0701 (15) | −0.0043 (14) | −0.0345 (13) | 0.0111 (13) |
C23 | 0.0800 (15) | 0.0773 (15) | 0.0849 (16) | 0.0115 (12) | −0.0256 (13) | 0.0150 (13) |
C24 | 0.0778 (14) | 0.0635 (12) | 0.0650 (13) | 0.0102 (11) | −0.0148 (11) | 0.0063 (10) |
C25 | 0.0611 (12) | 0.1042 (18) | 0.0708 (14) | −0.0241 (12) | 0.0196 (10) | −0.0172 (12) |
C26A | 0.0440 (18) | 0.124 (4) | 0.074 (2) | −0.007 (3) | −0.0019 (16) | 0.019 (3) |
C26B | 0.047 (4) | 0.090 (7) | 0.059 (5) | −0.013 (5) | 0.009 (3) | −0.009 (4) |
C27 | 0.0597 (12) | 0.1047 (17) | 0.0589 (12) | −0.0316 (12) | −0.0032 (10) | −0.0059 (12) |
C28 | 0.0487 (10) | 0.0578 (10) | 0.0467 (10) | −0.0079 (8) | 0.0012 (8) | −0.0079 (8) |
C29 | 0.0394 (8) | 0.0534 (10) | 0.0396 (8) | 0.0007 (8) | −0.0036 (7) | −0.0028 (7) |
C30 | 0.0451 (9) | 0.0564 (10) | 0.0397 (9) | −0.0064 (8) | −0.0020 (7) | −0.0064 (8) |
C31 | 0.0838 (14) | 0.0957 (16) | 0.0433 (11) | 0.0246 (13) | −0.0046 (10) | −0.0039 (10) |
C32 | 0.121 (2) | 0.119 (2) | 0.0403 (11) | 0.0281 (18) | −0.0017 (12) | −0.0009 (12) |
C33 | 0.0903 (16) | 0.1002 (18) | 0.0477 (12) | −0.0034 (14) | 0.0130 (11) | −0.0157 (11) |
C34 | 0.0605 (12) | 0.0898 (16) | 0.0658 (13) | 0.0040 (11) | 0.0090 (10) | −0.0210 (12) |
C35 | 0.0519 (10) | 0.0790 (13) | 0.0495 (10) | 0.0037 (10) | 0.0007 (8) | −0.0073 (9) |
O1—C8 | 1.2184 (19) | C19—C20 | 1.411 (2) |
N1—C25 | 1.450 (2) | C20—C21 | 1.408 (2) |
N1—C28 | 1.472 (2) | C21—C22 | 1.355 (3) |
N1—C10 | 1.473 (2) | C21—H21 | 0.9300 |
N2—C18 | 1.303 (2) | C22—C23 | 1.388 (3) |
N2—C19 | 1.380 (2) | C22—H22 | 0.9300 |
N3—C17 | 1.311 (2) | C23—C24 | 1.368 (3) |
N3—C20 | 1.378 (2) | C23—H23 | 0.9300 |
C1—C2 | 1.507 (2) | C24—H24 | 0.9300 |
C1—H1A | 0.9600 | C25—C26B | 1.464 (6) |
C1—H1B | 0.9600 | C25—C26A | 1.470 (4) |
C1—H1C | 0.9600 | C25—H25A | 0.9700 |
C2—C3 | 1.383 (3) | C25—H25B | 0.9700 |
C2—C7 | 1.387 (2) | C25—H25C | 0.9700 |
C3—C4 | 1.379 (3) | C25—H25D | 0.9700 |
C3—H3 | 0.9300 | C26A—C27 | 1.499 (4) |
C4—C5 | 1.387 (2) | C26A—H26A | 0.9700 |
C4—H4 | 0.9300 | C26A—H26B | 0.9700 |
C5—C6 | 1.383 (2) | C26B—C27 | 1.507 (6) |
C5—C8 | 1.493 (2) | C26B—H26C | 0.9700 |
C6—C7 | 1.384 (2) | C26B—H26D | 0.9700 |
C6—H6 | 0.9300 | C27—C28 | 1.526 (2) |
C7—H7 | 0.9300 | C27—H27A | 0.9700 |
C8—C9 | 1.516 (2) | C27—H27B | 0.9700 |
C9—C29 | 1.533 (2) | C27—H27C | 0.9700 |
C9—C10 | 1.577 (2) | C27—H27D | 0.9700 |
C9—H9 | 0.9800 | C28—C29 | 1.529 (2) |
C10—C18 | 1.525 (2) | C28—H28 | 0.9800 |
C10—C11 | 1.532 (2) | C29—C30 | 1.509 (2) |
C11—C16 | 1.382 (2) | C29—H29 | 0.9800 |
C11—C12 | 1.395 (2) | C30—C31 | 1.374 (2) |
C12—C13 | 1.386 (2) | C30—C35 | 1.381 (2) |
C12—C17 | 1.462 (2) | C31—C32 | 1.378 (3) |
C13—C14 | 1.384 (3) | C31—H31 | 0.9300 |
C13—H13 | 0.9300 | C32—C33 | 1.358 (3) |
C14—C15 | 1.381 (3) | C32—H32 | 0.9300 |
C14—H14 | 0.9300 | C33—C34 | 1.360 (3) |
C15—C16 | 1.381 (3) | C33—H33 | 0.9300 |
C15—H15 | 0.9300 | C34—C35 | 1.379 (3) |
C16—H16 | 0.9300 | C34—H34 | 0.9300 |
C17—C18 | 1.420 (2) | C35—H35 | 0.9300 |
C19—C24 | 1.408 (3) | ||
C25—N1—C28 | 109.48 (14) | C22—C23—H23 | 119.7 |
C25—N1—C10 | 122.45 (15) | C23—C24—C19 | 119.7 (2) |
C28—N1—C10 | 111.43 (12) | C23—C24—H24 | 120.1 |
C18—N2—C19 | 114.56 (14) | C19—C24—H24 | 120.1 |
C17—N3—C20 | 114.49 (15) | N1—C25—C26B | 107.1 (3) |
C2—C1—H1A | 109.5 | N1—C25—C26A | 105.2 (2) |
C2—C1—H1B | 109.5 | N1—C25—H25A | 110.7 |
H1A—C1—H1B | 109.5 | C26B—C25—H25A | 134.7 |
C2—C1—H1C | 109.5 | C26A—C25—H25A | 110.7 |
H1A—C1—H1C | 109.5 | N1—C25—H25B | 110.7 |
H1B—C1—H1C | 109.5 | C26B—C25—H25B | 79.3 |
C3—C2—C7 | 117.26 (16) | C26A—C25—H25B | 110.7 |
C3—C2—C1 | 121.29 (17) | H25A—C25—H25B | 108.8 |
C7—C2—C1 | 121.45 (17) | N1—C25—H25C | 110.3 |
C4—C3—C2 | 121.49 (17) | C26B—C25—H25C | 110.3 |
C4—C3—H3 | 119.3 | C26A—C25—H25C | 80.4 |
C2—C3—H3 | 119.3 | H25B—C25—H25C | 132.4 |
C3—C4—C5 | 121.05 (17) | N1—C25—H25D | 110.3 |
C3—C4—H4 | 119.5 | C26B—C25—H25D | 110.3 |
C5—C4—H4 | 119.5 | C26A—C25—H25D | 136.8 |
C6—C5—C4 | 117.91 (16) | H25A—C25—H25D | 78.9 |
C6—C5—C8 | 123.66 (15) | H25C—C25—H25D | 108.6 |
C4—C5—C8 | 118.43 (15) | C25—C26A—C27 | 106.2 (3) |
C5—C6—C7 | 120.68 (16) | C25—C26A—H26A | 110.5 |
C5—C6—H6 | 119.7 | C27—C26A—H26A | 110.5 |
C7—C6—H6 | 119.7 | C25—C26A—H26B | 110.5 |
C6—C7—C2 | 121.61 (17) | C27—C26A—H26B | 110.5 |
C6—C7—H7 | 119.2 | H26A—C26A—H26B | 108.7 |
C2—C7—H7 | 119.2 | C25—C26B—C27 | 106.1 (4) |
O1—C8—C5 | 120.02 (15) | C25—C26B—H26C | 110.5 |
O1—C8—C9 | 119.81 (15) | C27—C26B—H26C | 110.5 |
C5—C8—C9 | 120.18 (14) | C25—C26B—H26D | 110.5 |
C8—C9—C29 | 114.01 (13) | C27—C26B—H26D | 110.5 |
C8—C9—C10 | 114.25 (12) | H26C—C26B—H26D | 108.7 |
C29—C9—C10 | 103.91 (12) | C26A—C27—C28 | 102.8 (2) |
C8—C9—H9 | 108.1 | C26B—C27—C28 | 105.2 (3) |
C29—C9—H9 | 108.1 | C26A—C27—H27A | 111.2 |
C10—C9—H9 | 108.1 | C26B—C27—H27A | 134.8 |
N1—C10—C18 | 110.53 (13) | C28—C27—H27A | 111.2 |
N1—C10—C11 | 117.08 (13) | C26A—C27—H27B | 111.2 |
C18—C10—C11 | 100.57 (12) | C26B—C27—H27B | 80.5 |
N1—C10—C9 | 102.76 (12) | C28—C27—H27B | 111.2 |
C18—C10—C9 | 111.31 (12) | H27A—C27—H27B | 109.1 |
C11—C10—C9 | 114.85 (13) | C26A—C27—H27C | 81.8 |
C16—C11—C12 | 119.52 (17) | C26B—C27—H27C | 110.7 |
C16—C11—C10 | 129.12 (16) | C28—C27—H27C | 110.7 |
C12—C11—C10 | 111.36 (14) | H27B—C27—H27C | 131.5 |
C13—C12—C11 | 121.29 (17) | C26A—C27—H27D | 137.4 |
C13—C12—C17 | 129.65 (17) | C26B—C27—H27D | 110.7 |
C11—C12—C17 | 109.04 (15) | C28—C27—H27D | 110.7 |
C14—C13—C12 | 118.4 (2) | H27A—C27—H27D | 80.6 |
C14—C13—H13 | 120.8 | H27C—C27—H27D | 108.8 |
C12—C13—H13 | 120.8 | N1—C28—C27 | 105.81 (14) |
C15—C14—C13 | 120.4 (2) | N1—C28—C29 | 105.24 (13) |
C15—C14—H14 | 119.8 | C27—C28—C29 | 117.17 (16) |
C13—C14—H14 | 119.8 | N1—C28—H28 | 109.4 |
C14—C15—C16 | 121.2 (2) | C27—C28—H28 | 109.4 |
C14—C15—H15 | 119.4 | C29—C28—H28 | 109.4 |
C16—C15—H15 | 119.4 | C30—C29—C28 | 114.60 (14) |
C15—C16—C11 | 119.19 (19) | C30—C29—C9 | 114.75 (13) |
C15—C16—H16 | 120.4 | C28—C29—C9 | 101.58 (12) |
C11—C16—H16 | 120.4 | C30—C29—H29 | 108.5 |
N3—C17—C18 | 123.40 (16) | C28—C29—H29 | 108.5 |
N3—C17—C12 | 128.77 (15) | C9—C29—H29 | 108.5 |
C18—C17—C12 | 107.82 (14) | C31—C30—C35 | 116.95 (16) |
N2—C18—C17 | 123.76 (14) | C31—C30—C29 | 121.17 (16) |
N2—C18—C10 | 125.07 (14) | C35—C30—C29 | 121.88 (15) |
C17—C18—C10 | 111.13 (14) | C30—C31—C32 | 121.4 (2) |
N2—C19—C24 | 118.70 (16) | C30—C31—H31 | 119.3 |
N2—C19—C20 | 121.78 (16) | C32—C31—H31 | 119.3 |
C24—C19—C20 | 119.51 (16) | C33—C32—C31 | 120.7 (2) |
N3—C20—C21 | 119.38 (17) | C33—C32—H32 | 119.6 |
N3—C20—C19 | 121.89 (15) | C31—C32—H32 | 119.6 |
C21—C20—C19 | 118.70 (18) | C32—C33—C34 | 119.07 (19) |
C22—C21—C20 | 120.5 (2) | C32—C33—H33 | 120.5 |
C22—C21—H21 | 119.7 | C34—C33—H33 | 120.5 |
C20—C21—H21 | 119.7 | C33—C34—C35 | 120.5 (2) |
C21—C22—C23 | 120.8 (2) | C33—C34—H34 | 119.8 |
C21—C22—H22 | 119.6 | C35—C34—H34 | 119.8 |
C23—C22—H22 | 119.6 | C34—C35—C30 | 121.40 (18) |
C24—C23—C22 | 120.7 (2) | C34—C35—H35 | 119.3 |
C24—C23—H23 | 119.7 | C30—C35—H35 | 119.3 |
C7—C2—C3—C4 | −1.2 (3) | C11—C10—C18—N2 | −175.19 (15) |
C1—C2—C3—C4 | 178.60 (18) | C9—C10—C18—N2 | −53.1 (2) |
C2—C3—C4—C5 | 1.2 (3) | N1—C10—C18—C17 | −121.43 (14) |
C3—C4—C5—C6 | −0.3 (3) | C11—C10—C18—C17 | 2.92 (16) |
C3—C4—C5—C8 | −179.86 (17) | C9—C10—C18—C17 | 125.04 (14) |
C4—C5—C6—C7 | −0.6 (2) | C18—N2—C19—C24 | −177.85 (16) |
C8—C5—C6—C7 | 178.94 (15) | C18—N2—C19—C20 | 1.2 (2) |
C5—C6—C7—C2 | 0.6 (3) | C17—N3—C20—C21 | −179.83 (17) |
C3—C2—C7—C6 | 0.3 (3) | C17—N3—C20—C19 | 2.1 (2) |
C1—C2—C7—C6 | −179.50 (17) | N2—C19—C20—N3 | −3.4 (3) |
C6—C5—C8—O1 | −168.12 (16) | C24—C19—C20—N3 | 175.65 (17) |
C4—C5—C8—O1 | 11.4 (2) | N2—C19—C20—C21 | 178.59 (17) |
C6—C5—C8—C9 | 12.4 (2) | C24—C19—C20—C21 | −2.4 (3) |
C4—C5—C8—C9 | −168.10 (15) | N3—C20—C21—C22 | −176.3 (2) |
O1—C8—C9—C29 | 22.8 (2) | C19—C20—C21—C22 | 1.8 (3) |
C5—C8—C9—C29 | −157.73 (13) | C20—C21—C22—C23 | 0.5 (4) |
O1—C8—C9—C10 | −96.54 (17) | C21—C22—C23—C24 | −2.2 (4) |
C5—C8—C9—C10 | 82.97 (17) | C22—C23—C24—C19 | 1.5 (3) |
C25—N1—C10—C18 | 101.23 (19) | N2—C19—C24—C23 | 179.85 (19) |
C28—N1—C10—C18 | −126.38 (14) | C20—C19—C24—C23 | 0.8 (3) |
C25—N1—C10—C11 | −13.1 (2) | C28—N1—C25—C26B | 17.7 (7) |
C28—N1—C10—C11 | 119.32 (15) | C10—N1—C25—C26B | 150.9 (7) |
C25—N1—C10—C9 | −139.91 (17) | C28—N1—C25—C26A | −17.1 (4) |
C28—N1—C10—C9 | −7.53 (16) | C10—N1—C25—C26A | 116.0 (4) |
C8—C9—C10—N1 | 153.63 (13) | N1—C25—C26A—C27 | 30.8 (6) |
C29—C9—C10—N1 | 28.79 (15) | C26B—C25—C26A—C27 | −67.3 (6) |
C8—C9—C10—C18 | −88.06 (16) | N1—C25—C26B—C27 | −25.4 (10) |
C29—C9—C10—C18 | 147.10 (13) | C26A—C25—C26B—C27 | 66.4 (6) |
C8—C9—C10—C11 | 25.37 (18) | C25—C26A—C27—C26B | 66.4 (5) |
C29—C9—C10—C11 | −99.47 (15) | C25—C26A—C27—C28 | −31.9 (5) |
N1—C10—C11—C16 | −62.9 (2) | C25—C26B—C27—C26A | −66.8 (6) |
C18—C10—C11—C16 | 177.41 (17) | C25—C26B—C27—C28 | 23.3 (10) |
C9—C10—C11—C16 | 57.8 (2) | C25—N1—C28—C27 | −2.8 (2) |
N1—C10—C11—C12 | 117.55 (16) | C10—N1—C28—C27 | −141.40 (16) |
C18—C10—C11—C12 | −2.19 (17) | C25—N1—C28—C29 | 121.90 (17) |
C9—C10—C11—C12 | −121.78 (15) | C10—N1—C28—C29 | −16.71 (17) |
C16—C11—C12—C13 | −0.2 (3) | C26A—C27—C28—N1 | 21.0 (4) |
C10—C11—C12—C13 | 179.43 (16) | C26B—C27—C28—N1 | −12.6 (6) |
C16—C11—C12—C17 | −178.88 (16) | C26A—C27—C28—C29 | −95.9 (3) |
C10—C11—C12—C17 | 0.76 (19) | C26B—C27—C28—C29 | −129.5 (6) |
C11—C12—C13—C14 | 0.0 (3) | N1—C28—C29—C30 | 158.35 (13) |
C17—C12—C13—C14 | 178.36 (18) | C27—C28—C29—C30 | −84.43 (19) |
C12—C13—C14—C15 | 0.4 (3) | N1—C28—C29—C9 | 34.03 (16) |
C13—C14—C15—C16 | −0.7 (4) | C27—C28—C29—C9 | 151.25 (16) |
C14—C15—C16—C11 | 0.5 (3) | C8—C9—C29—C30 | 72.33 (18) |
C12—C11—C16—C15 | 0.0 (3) | C10—C9—C29—C30 | −162.67 (14) |
C10—C11—C16—C15 | −179.59 (18) | C8—C9—C29—C28 | −163.45 (13) |
C20—N3—C17—C18 | 0.9 (2) | C10—C9—C29—C28 | −38.46 (15) |
C20—N3—C17—C12 | −177.45 (16) | C28—C29—C30—C31 | 116.83 (19) |
C13—C12—C17—N3 | 1.2 (3) | C9—C29—C30—C31 | −126.17 (19) |
C11—C12—C17—N3 | 179.73 (17) | C28—C29—C30—C35 | −62.5 (2) |
C13—C12—C17—C18 | −177.35 (18) | C9—C29—C30—C35 | 54.5 (2) |
C11—C12—C17—C18 | 1.17 (19) | C35—C30—C31—C32 | 0.1 (3) |
C19—N2—C18—C17 | 1.9 (2) | C29—C30—C31—C32 | −179.2 (2) |
C19—N2—C18—C10 | 179.80 (14) | C30—C31—C32—C33 | −0.5 (4) |
N3—C17—C18—N2 | −3.2 (3) | C31—C32—C33—C34 | 0.4 (4) |
C12—C17—C18—N2 | 175.48 (15) | C32—C33—C34—C35 | 0.0 (4) |
N3—C17—C18—C10 | 178.68 (15) | C33—C34—C35—C30 | −0.4 (3) |
C12—C17—C18—C10 | −2.67 (18) | C31—C30—C35—C34 | 0.3 (3) |
N1—C10—C18—N2 | 60.5 (2) | C29—C30—C35—C34 | 179.62 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···O1i | 0.96 | 2.56 | 3.483 (2) | 161 |
C22—H22···O1ii | 0.93 | 2.48 | 3.361 (3) | 158 |
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+1/2, −y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C35H29N3O |
Mr | 507.61 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 16.4102 (6), 16.4371 (6), 20.0648 (7) |
V (Å3) | 5412.2 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 47718, 6643, 3751 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.144, 1.01 |
No. of reflections | 6643 |
No. of parameters | 363 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.25 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···O1i | 0.96 | 2.56 | 3.483 (2) | 161 |
C22—H22···O1ii | 0.93 | 2.48 | 3.361 (3) | 158 |
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+1/2, −y, z+1/2. |
Acknowledgements
TS and DV thank TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for data collection and TS thanks DST for an Inspire fellowship.
References
Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–409. Web of Science PubMed Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gayathri, D., Aravindan, P. G., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2005). Acta Cryst. E61, o3124–o3126. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zarranz, B., Jago, A., Aldana, I. & Monge, A. (2003). Bioorg. Med. Chem. 11, 2149–2156. Web of Science CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Pyrrolidine derivatives are found to have anticonvulsant, antimicrobial and antifungal activities against various pathogens (Amal Raj et al., 2003). Quinoxaline derivatives shown antibacterial, antiviral and anticancer properties (Zarranz et al., 2003). As spiro pyrrolidine compounds are of great medicinal properties, we have undertaken the three dimensional structure of the title compound.
X-ray analysis confirms the molecular structure and atom connectivity of the compound as illustrated in Fig. 1. The quinoxaline moiety is essentially planar with a maximum deviation of -0.0472 (23) Å for C21 atom, and it forms the dihedral angles of 4.75 (3), 54.94 (5) and 29.70 (6) ° with the indene moiety, phenyl rings (C2–C7) and (C30–C35), respectively. The indene moiety is also essentially planar with a maximum deviation of 0.0320 (16) Å for C18 atom, and it forms the dihedral angles of 51.75 (6) and 32.41 (6) ° with the phenyl rings (C2–C7) and (C30–C35), respectively.
The pyrrolizine moiety is folded and twisted about the N—C bond common to the two five membered rings. The indene fused with quinoxaline, subsituted five membered ring adopts twisted conformation on C9 and C29 atoms with the puckering parameters of Q2 = 0.3846 (17) Å, φ2 = 95.8 (3) °. The unsubsituted five-membered ring has a disordered C atom with occupancy factor of 0.676 (12)/0.324 (12). The five-membered ring (N1/C25/C26A/C27/C28) adopts an envelope conformation on C26A for major occupancy atom with the puckering parameters Q2 = 0.309 (4) Å, φ2 = 77.9 (5) °. The five-membered ring (N1/C25/C26B/C27/C28) adopts an envelope conformation on C26B for minor occupancy atom with the puckering parameters Q2 = 0.238 (6) Å, φ2 = 247.0 (10) °. The title compound exhibits structural similarities with the already reported related structures (Gayathri et al.2005).
In the crystal packing, molecules are linked via bifurcated C—H···O intermolecular hydrogen bonds involving the carbonyl group O atom as a single acceptor (Table. 1). The packing view of the compound is shown in Fig. 2.