organic compounds
6a-Nitro-6-(2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)-6a,6b,7,8,9,11a-hexahydro-6H-spiro[chromeno[3,4-a]pyrrolizine-11,11′-indeno[1,2-b]quinoxaline]
aPost Graduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: seshadri_pr@yahoo.com
In the title compound, C39H38N4O8, the quinoxaline and indene subunits are essentially planar, with maximum deviations of 0.071 (2) and 0.009 (2) Å, respectively. The indenoquinoxaline system forms a dihedral angle of 72.81 (3)° with the chromenopyrrolizine system. The two dioxolane rings, as well as the pyran ring of the chromeno group and the terminal pyrrolizine, each adopt an with O and C as flap atoms. The central pyrrolizine ring adopts a twisted conformation. Intramolecular C—H⋯O and C—H⋯N hydrogen bonds occur. The exhibits C—H⋯O hydrogen bonds, and is further stablized by C—H⋯π interactions, forming a two-dimensional network along the bc plane.
CCDC reference: 974343
Related literature
For some et al. (1991); James et al. (1991). For the pharmaceutical importance of quinoxaline derivatives, see: Seitz et al. (2002); He et al. (2003). For conformation analysis, see: Cremer & Pople (1975).
of biological importance, see: KobayashiExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; 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); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 974343
https://doi.org/10.1107/S1600536813032467/im2440sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032467/im2440Isup2.hkl
To a solution of 11H-indeno[1,2-b]quinoxalin-11-one (0.3 g, 1.29 mmol) and proline (0.208 g, 1.8 mmol) in dry acetonitrile, was added 2,2,7,7-tetramethyl-5-(3-nitro-2H-chromen-2-yl)tetrahydro-3aH-bis[1,3] dioxolo[4,5 - b:4',5'-d]pyran (0.52 g, 1.29 mmol) under a nitrogen atmosphere. The reaction mixture was refluxed for 16 h in a Dean-Stark apparatus to give the cycloadduct. After completion of the reaction as indicated by TLC, the solvent was evaporated under reduced pressure. The crude product was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate and concentrated in vacuo. Then the crude product was purified by
using hexane/EtOAc (7:3) as (yield: 0.7 g, 80%). Colourless block shaped crystals were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.Hydrogen atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 - 0.97 Å and Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for other H atoms.
Spiro compounds are a particular class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). Quinoxaline derivatives are an important class of benzoheterocycles. They have found applications as anticancer, antiviral, and antibacterial agents (Seitz et al., 2002; He et al., 2003).
In the title compound, C39H38N4O8, the quinoxaline (C7—C14\N1\N2) and indene (C1—C7\C14\C15) subunits are essentially planar with maximum deviations of -0.071 (2) Å for C14 and -0.009 (1) Å for C9, respectively. The dihedral angle between the chromeno-pyrrolizine (C15—C28\N2\N3\O1) and indeno-quinoxaline (C—C15\N1\N2) systems is 72.81 (3)° showing their almost orthogonal arrangement relative to each other.
The two dioxolane rings (C30—C32\O5\O6,C33—C35\O7\O8) which are fused with a pyran ring adopt an Φ2 = 108.05 (2)° and q2 = 0.2905 (1) Å, Φ2 = 324.14 (2)°, respectively. The pyran ring (C20—C22\C27\C28\O1) of the chromeno group and the pyrrolizine ring (C16—C19\N3) also adopt envelope conformations with O1 and C16 atoms as the flap. Puckering parameters are q2 = 0.3895 (1) Å, q3 = -0.2566 Å, Φ2 = 235.74 (2)°, Θ = 123.38° for the pyran and q2 = 0.3781 (1) Å, Φ2 = 213.99 (4)° for the pyrrolizine system, respectively. The pyrrolizine ring fused with the pyran ring adopts a twisted conformation along N3—C15 with puckering parameters of q2 = 0.301 (1) Å, Φ2 = 200.75 (2)° (Cremer & Pople, 1975).
with O6 and C34 atoms as the flap. Puckering parameters are q2 = 0.3089 (1) Å,The structure is stabilized by an intermolecular C—H···O hydrogen bond and additional intramolecular C—H···O and C—H···N hydrogen bonds (Table 1). The
is further consolidated by C—H ···Cg8 interactions where Cg8 is the centroid of C7\C8\C13\C14\N1\N2 ring.For some
of biological importance, see: Kobayashi et al. (1991); James et al. (1991). For the pharmaceutical importance of quinoxaline derivatives, see: Seitz et al. (2002); He et al. (2003). For conformation analysis, see: Cremer & Pople (1975).Data collection: APEX2 (Bruker, 2008); cell
SAINT (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 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. Molecular structure of the title compound showing 30% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radius. | |
Fig. 2. A view of packing of the molecules with hydrogen bonds (dashed lines). |
C39H38N4O8 | F(000) = 1456 |
Mr = 690.73 | Dx = 1.336 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 8626 reflections |
a = 11.3150 (9) Å | θ = 1.7–28.4° |
b = 15.629 (2) Å | µ = 0.09 mm−1 |
c = 19.419 (2) Å | T = 293 K |
V = 3434.0 (6) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.15 × 0.10 mm |
Bruker Kappa APEXII CCD diffractometer | 6671 independent reflections |
Radiation source: fine-focus sealed tube | 3789 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω and φ scan | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −13→13 |
Tmin = 0.981, Tmax = 0.991 | k = −19→18 |
15819 measured reflections | l = −23→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.047P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
6671 reflections | Δρmax = 0.17 e Å−3 |
460 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2933 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.30 (13) |
C39H38N4O8 | V = 3434.0 (6) Å3 |
Mr = 690.73 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 11.3150 (9) Å | µ = 0.09 mm−1 |
b = 15.629 (2) Å | T = 293 K |
c = 19.419 (2) Å | 0.20 × 0.15 × 0.10 mm |
Bruker Kappa APEXII CCD diffractometer | 6671 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 3789 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.991 | Rint = 0.059 |
15819 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.124 | Δρmax = 0.17 e Å−3 |
S = 0.97 | Δρmin = −0.20 e Å−3 |
6671 reflections | Absolute structure: Flack (1983), 2933 Friedel pairs |
460 parameters | Absolute structure parameter: 0.30 (13) |
0 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
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 | ||
O1 | 0.03697 (19) | 0.83284 (16) | −0.00002 (10) | 0.0524 (6) | |
O2 | −0.1751 (2) | 0.73787 (18) | 0.04849 (14) | 0.0690 (8) | |
O3 | −0.3060 (2) | 0.8322 (2) | 0.07234 (15) | 0.0819 (9) | |
O4 | 0.00221 (19) | 0.73589 (14) | 0.16455 (9) | 0.0450 (5) | |
O5 | −0.0801 (2) | 0.60162 (17) | 0.15228 (13) | 0.0645 (7) | |
O6 | 0.0907 (2) | 0.55340 (17) | 0.10693 (13) | 0.0635 (7) | |
O7 | 0.2843 (2) | 0.68893 (18) | 0.20258 (12) | 0.0672 (7) | |
O8 | 0.23002 (19) | 0.81048 (15) | 0.14967 (12) | 0.0568 (7) | |
N1 | 0.0704 (3) | 1.2133 (2) | 0.11551 (13) | 0.0563 (8) | |
N2 | 0.0858 (2) | 1.03075 (19) | 0.13143 (14) | 0.0522 (7) | |
N3 | −0.1654 (2) | 0.98556 (18) | 0.16878 (13) | 0.0428 (7) | |
N4 | −0.2032 (3) | 0.8083 (2) | 0.06782 (14) | 0.0507 (7) | |
C1 | −0.2053 (3) | 1.1070 (2) | 0.08517 (16) | 0.0484 (9) | |
C2 | −0.3219 (3) | 1.1091 (3) | 0.06145 (19) | 0.0643 (11) | |
H2 | −0.3667 | 1.0593 | 0.0587 | 0.077* | |
C3 | −0.3687 (4) | 1.1872 (3) | 0.0422 (2) | 0.0722 (12) | |
H3 | −0.4460 | 1.1893 | 0.0261 | 0.087* | |
C4 | −0.3057 (4) | 1.2611 (3) | 0.0460 (2) | 0.0744 (12) | |
H4 | −0.3407 | 1.3127 | 0.0337 | 0.089* | |
C5 | −0.1888 (4) | 1.2597 (3) | 0.06840 (18) | 0.0631 (10) | |
H5 | −0.1443 | 1.3096 | 0.0705 | 0.076* | |
C6 | −0.1408 (3) | 1.1816 (2) | 0.08745 (15) | 0.0485 (9) | |
C7 | −0.0190 (3) | 1.1607 (2) | 0.10770 (15) | 0.0450 (8) | |
C8 | 0.1751 (3) | 1.1725 (3) | 0.13211 (17) | 0.0559 (10) | |
C9 | 0.2774 (4) | 1.2228 (3) | 0.1405 (2) | 0.0753 (13) | |
H9 | 0.2739 | 1.2818 | 0.1346 | 0.090* | |
C10 | 0.3812 (4) | 1.1847 (4) | 0.1572 (2) | 0.0878 (15) | |
H10 | 0.4482 | 1.2182 | 0.1637 | 0.105* | |
C11 | 0.3893 (4) | 1.0961 (4) | 0.1649 (3) | 0.0977 (16) | |
H11 | 0.4614 | 1.0712 | 0.1760 | 0.117* | |
C12 | 0.2919 (3) | 1.0457 (3) | 0.1562 (2) | 0.0832 (13) | |
H12 | 0.2977 | 0.9867 | 0.1610 | 0.100* | |
C13 | 0.1827 (3) | 1.0838 (3) | 0.13974 (18) | 0.0556 (10) | |
C14 | −0.0112 (3) | 1.0707 (2) | 0.11541 (15) | 0.0438 (8) | |
C15 | −0.1313 (3) | 1.0280 (2) | 0.10405 (15) | 0.0428 (8) | |
C16 | −0.2921 (3) | 0.9806 (3) | 0.18833 (17) | 0.0554 (10) | |
H16A | −0.3413 | 0.9653 | 0.1493 | 0.067* | |
H16B | −0.3198 | 1.0341 | 0.2078 | 0.067* | |
C17 | −0.2893 (3) | 0.9102 (3) | 0.24158 (18) | 0.0608 (10) | |
H17A | −0.3663 | 0.8834 | 0.2457 | 0.073* | |
H17B | −0.2664 | 0.9327 | 0.2862 | 0.073* | |
C18 | −0.1979 (3) | 0.8461 (3) | 0.21548 (16) | 0.0575 (10) | |
H18A | −0.2359 | 0.7992 | 0.1914 | 0.069* | |
H18B | −0.1520 | 0.8230 | 0.2534 | 0.069* | |
C19 | −0.1189 (3) | 0.8974 (2) | 0.16643 (14) | 0.0410 (8) | |
H19 | −0.0391 | 0.8983 | 0.1859 | 0.049* | |
C20 | −0.1080 (3) | 0.8724 (2) | 0.08846 (15) | 0.0402 (8) | |
C21 | 0.0170 (3) | 0.8386 (2) | 0.07265 (14) | 0.0385 (7) | |
H21 | 0.0735 | 0.8803 | 0.0911 | 0.046* | |
C22 | 0.0241 (3) | 0.9087 (2) | −0.03512 (15) | 0.0440 (8) | |
C23 | 0.0911 (3) | 0.9177 (3) | −0.09451 (17) | 0.0596 (10) | |
H23 | 0.1434 | 0.8749 | −0.1078 | 0.071* | |
C24 | 0.0793 (4) | 0.9897 (3) | −0.13301 (18) | 0.0666 (11) | |
H24 | 0.1243 | 0.9965 | −0.1727 | 0.080* | |
C25 | 0.0006 (4) | 1.0533 (3) | −0.11346 (18) | 0.0685 (11) | |
H25 | −0.0068 | 1.1026 | −0.1399 | 0.082* | |
C26 | −0.0667 (3) | 1.0433 (2) | −0.05465 (16) | 0.0565 (10) | |
H26 | −0.1201 | 1.0857 | −0.0421 | 0.068* | |
C27 | −0.0553 (3) | 0.9703 (2) | −0.01397 (14) | 0.0426 (8) | |
C28 | −0.1323 (3) | 0.9566 (2) | 0.04885 (15) | 0.0426 (8) | |
H28 | −0.2138 | 0.9528 | 0.0320 | 0.051* | |
C29 | 0.0536 (3) | 0.7508 (2) | 0.09899 (15) | 0.0410 (8) | |
H29 | 0.0258 | 0.7070 | 0.0667 | 0.049* | |
C30 | 0.0092 (3) | 0.6504 (2) | 0.18407 (17) | 0.0519 (9) | |
H30 | −0.0012 | 0.6468 | 0.2341 | 0.062* | |
C31 | −0.0300 (3) | 0.5300 (3) | 0.1170 (2) | 0.0649 (11) | |
C32 | 0.1236 (3) | 0.6036 (2) | 0.16469 (18) | 0.0553 (9) | |
H32 | 0.1489 | 0.5665 | 0.2026 | 0.066* | |
C33 | 0.2250 (3) | 0.6609 (2) | 0.14226 (18) | 0.0516 (9) | |
H33 | 0.2796 | 0.6288 | 0.1129 | 0.062* | |
C34 | 0.3182 (3) | 0.7751 (3) | 0.19214 (18) | 0.0590 (10) | |
C35 | 0.1876 (3) | 0.7440 (2) | 0.10601 (16) | 0.0445 (8) | |
H35 | 0.2251 | 0.7479 | 0.0606 | 0.053* | |
C36 | −0.0875 (4) | 0.5211 (3) | 0.0485 (2) | 0.0846 (13) | |
H36A | −0.1688 | 0.5053 | 0.0545 | 0.127* | |
H36B | −0.0476 | 0.4776 | 0.0224 | 0.127* | |
H36C | −0.0831 | 0.5745 | 0.0243 | 0.127* | |
C37 | −0.0398 (4) | 0.4515 (3) | 0.1621 (2) | 0.0955 (15) | |
H37A | −0.1215 | 0.4370 | 0.1681 | 0.143* | |
H37B | −0.0048 | 0.4631 | 0.2061 | 0.143* | |
H37C | 0.0008 | 0.4047 | 0.1406 | 0.143* | |
C38 | 0.4382 (3) | 0.7814 (3) | 0.1578 (2) | 0.0901 (15) | |
H38A | 0.4587 | 0.8405 | 0.1517 | 0.135* | |
H38B | 0.4354 | 0.7536 | 0.1137 | 0.135* | |
H38C | 0.4965 | 0.7541 | 0.1862 | 0.135* | |
C39 | 0.3150 (4) | 0.8192 (3) | 0.2610 (2) | 0.0891 (15) | |
H39A | 0.3377 | 0.8780 | 0.2555 | 0.134* | |
H39B | 0.3689 | 0.7914 | 0.2920 | 0.134* | |
H39C | 0.2364 | 0.8164 | 0.2795 | 0.134* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0671 (15) | 0.0485 (16) | 0.0417 (12) | 0.0044 (13) | 0.0116 (12) | 0.0053 (11) |
O2 | 0.0695 (17) | 0.0440 (18) | 0.093 (2) | −0.0040 (14) | −0.0303 (15) | −0.0075 (15) |
O3 | 0.0404 (15) | 0.086 (2) | 0.120 (2) | −0.0129 (15) | 0.0069 (15) | −0.0265 (18) |
O4 | 0.0532 (13) | 0.0413 (14) | 0.0403 (11) | 0.0031 (11) | 0.0078 (11) | 0.0071 (10) |
O5 | 0.0573 (15) | 0.0536 (18) | 0.0828 (17) | −0.0092 (14) | 0.0014 (14) | −0.0015 (14) |
O6 | 0.0593 (16) | 0.0528 (17) | 0.0785 (17) | −0.0045 (13) | −0.0014 (14) | −0.0130 (13) |
O7 | 0.0681 (17) | 0.061 (2) | 0.0721 (17) | −0.0002 (15) | −0.0298 (14) | 0.0014 (14) |
O8 | 0.0506 (14) | 0.0506 (16) | 0.0693 (15) | −0.0014 (12) | −0.0141 (12) | −0.0111 (13) |
N1 | 0.061 (2) | 0.053 (2) | 0.0542 (18) | −0.0164 (17) | 0.0069 (15) | −0.0056 (15) |
N2 | 0.0402 (16) | 0.054 (2) | 0.0624 (18) | −0.0037 (16) | −0.0054 (14) | −0.0007 (15) |
N3 | 0.0354 (15) | 0.0474 (19) | 0.0456 (15) | −0.0028 (13) | 0.0002 (12) | −0.0001 (14) |
N4 | 0.053 (2) | 0.053 (2) | 0.0467 (16) | −0.0075 (17) | −0.0057 (15) | 0.0020 (15) |
C1 | 0.047 (2) | 0.053 (2) | 0.0453 (19) | 0.0040 (19) | −0.0004 (17) | 0.0011 (18) |
C2 | 0.053 (2) | 0.067 (3) | 0.073 (2) | 0.006 (2) | −0.012 (2) | 0.005 (2) |
C3 | 0.064 (2) | 0.082 (4) | 0.071 (3) | 0.020 (3) | −0.010 (2) | 0.004 (3) |
C4 | 0.085 (3) | 0.068 (3) | 0.071 (3) | 0.031 (3) | −0.005 (2) | 0.001 (2) |
C5 | 0.077 (3) | 0.046 (2) | 0.066 (2) | 0.010 (2) | 0.000 (2) | 0.0013 (19) |
C6 | 0.058 (2) | 0.045 (2) | 0.0419 (19) | 0.0076 (19) | 0.0032 (16) | −0.0001 (17) |
C7 | 0.053 (2) | 0.042 (2) | 0.0400 (17) | −0.0013 (19) | 0.0053 (16) | −0.0043 (16) |
C8 | 0.050 (2) | 0.067 (3) | 0.051 (2) | −0.014 (2) | 0.0076 (18) | −0.010 (2) |
C9 | 0.064 (3) | 0.083 (3) | 0.079 (3) | −0.029 (3) | 0.015 (2) | −0.017 (2) |
C10 | 0.053 (3) | 0.112 (5) | 0.099 (3) | −0.026 (3) | 0.004 (2) | −0.019 (3) |
C11 | 0.041 (3) | 0.125 (5) | 0.126 (4) | −0.005 (3) | −0.010 (3) | −0.006 (4) |
C12 | 0.043 (2) | 0.088 (3) | 0.119 (4) | −0.001 (2) | −0.011 (2) | −0.001 (3) |
C13 | 0.045 (2) | 0.063 (3) | 0.058 (2) | −0.009 (2) | −0.0004 (18) | −0.0048 (19) |
C14 | 0.045 (2) | 0.046 (2) | 0.0395 (18) | −0.0041 (17) | 0.0020 (16) | −0.0048 (16) |
C15 | 0.0364 (17) | 0.045 (2) | 0.0472 (19) | −0.0039 (16) | −0.0029 (15) | 0.0032 (17) |
C16 | 0.0368 (19) | 0.070 (3) | 0.060 (2) | −0.0058 (19) | 0.0071 (17) | −0.007 (2) |
C17 | 0.051 (2) | 0.074 (3) | 0.056 (2) | −0.008 (2) | 0.0116 (19) | −0.002 (2) |
C18 | 0.065 (2) | 0.063 (3) | 0.0441 (19) | −0.006 (2) | 0.0124 (18) | −0.0006 (18) |
C19 | 0.0402 (18) | 0.045 (2) | 0.0373 (16) | −0.0035 (16) | 0.0006 (15) | −0.0018 (15) |
C20 | 0.0385 (18) | 0.041 (2) | 0.0415 (17) | −0.0098 (15) | 0.0005 (15) | −0.0001 (15) |
C21 | 0.0418 (18) | 0.039 (2) | 0.0352 (16) | −0.0026 (16) | 0.0034 (14) | 0.0011 (15) |
C22 | 0.051 (2) | 0.044 (2) | 0.0359 (17) | −0.0040 (18) | −0.0014 (17) | 0.0072 (16) |
C23 | 0.061 (2) | 0.066 (3) | 0.052 (2) | 0.001 (2) | 0.0160 (19) | 0.006 (2) |
C24 | 0.077 (3) | 0.073 (3) | 0.050 (2) | −0.006 (2) | 0.013 (2) | 0.018 (2) |
C25 | 0.084 (3) | 0.069 (3) | 0.052 (2) | −0.007 (2) | −0.002 (2) | 0.023 (2) |
C26 | 0.062 (2) | 0.058 (3) | 0.050 (2) | 0.002 (2) | −0.0056 (19) | 0.0097 (19) |
C27 | 0.0442 (18) | 0.048 (2) | 0.0358 (17) | −0.0064 (18) | −0.0048 (15) | 0.0047 (16) |
C28 | 0.0380 (17) | 0.045 (2) | 0.0453 (18) | −0.0051 (16) | −0.0056 (15) | 0.0019 (16) |
C29 | 0.0442 (19) | 0.041 (2) | 0.0376 (17) | 0.0016 (16) | 0.0054 (15) | −0.0015 (15) |
C30 | 0.058 (2) | 0.053 (2) | 0.0449 (18) | −0.005 (2) | −0.0010 (18) | 0.0054 (17) |
C31 | 0.059 (2) | 0.048 (3) | 0.088 (3) | −0.004 (2) | −0.006 (2) | 0.000 (2) |
C32 | 0.060 (2) | 0.047 (2) | 0.059 (2) | 0.0036 (19) | −0.0098 (19) | 0.002 (2) |
C33 | 0.0454 (19) | 0.050 (2) | 0.059 (2) | 0.0082 (18) | −0.0054 (18) | −0.0081 (19) |
C34 | 0.051 (2) | 0.063 (3) | 0.064 (2) | 0.009 (2) | −0.0115 (19) | −0.010 (2) |
C35 | 0.0448 (19) | 0.047 (2) | 0.0415 (17) | −0.0003 (17) | 0.0038 (15) | −0.0055 (17) |
C36 | 0.077 (3) | 0.085 (3) | 0.092 (3) | −0.010 (3) | −0.017 (3) | −0.013 (3) |
C37 | 0.102 (4) | 0.059 (3) | 0.126 (4) | −0.014 (3) | −0.013 (3) | 0.011 (3) |
C38 | 0.051 (3) | 0.101 (4) | 0.119 (4) | −0.001 (2) | −0.002 (3) | −0.020 (3) |
C39 | 0.098 (3) | 0.094 (4) | 0.076 (3) | 0.012 (3) | −0.028 (3) | −0.025 (3) |
O1—C22 | 1.376 (4) | C17—C18 | 1.527 (5) |
O1—C21 | 1.432 (3) | C17—H17A | 0.9700 |
O2—N4 | 1.205 (4) | C17—H17B | 0.9700 |
O3—N4 | 1.225 (4) | C18—C19 | 1.533 (4) |
O4—C30 | 1.391 (4) | C18—H18A | 0.9700 |
O4—C29 | 1.419 (3) | C18—H18B | 0.9700 |
O5—C30 | 1.408 (4) | C19—C20 | 1.569 (4) |
O5—C31 | 1.429 (5) | C19—H19 | 0.9800 |
O6—C32 | 1.419 (4) | C20—C21 | 1.541 (4) |
O6—C31 | 1.427 (4) | C20—C28 | 1.549 (4) |
O7—C34 | 1.414 (5) | C21—C29 | 1.522 (4) |
O7—C33 | 1.419 (4) | C21—H21 | 0.9800 |
O8—C34 | 1.408 (4) | C22—C27 | 1.379 (4) |
O8—C35 | 1.424 (4) | C22—C23 | 1.387 (4) |
N1—C7 | 1.313 (4) | C23—C24 | 1.358 (5) |
N1—C8 | 1.383 (5) | C23—H23 | 0.9300 |
N2—C14 | 1.301 (4) | C24—C25 | 1.386 (6) |
N2—C13 | 1.384 (4) | C24—H24 | 0.9300 |
N3—C15 | 1.473 (4) | C25—C26 | 1.381 (5) |
N3—C19 | 1.475 (4) | C25—H25 | 0.9300 |
N3—C16 | 1.486 (4) | C26—C27 | 1.394 (5) |
N4—C20 | 1.524 (4) | C26—H26 | 0.9300 |
C1—C6 | 1.376 (5) | C27—C28 | 1.514 (4) |
C1—C2 | 1.397 (5) | C28—H28 | 0.9800 |
C1—C15 | 1.537 (5) | C29—C35 | 1.526 (4) |
C2—C3 | 1.382 (5) | C29—H29 | 0.9800 |
C2—H2 | 0.9300 | C30—C32 | 1.534 (5) |
C3—C4 | 1.359 (6) | C30—H30 | 0.9800 |
C3—H3 | 0.9300 | C31—C36 | 1.488 (5) |
C4—C5 | 1.392 (6) | C31—C37 | 1.510 (5) |
C4—H4 | 0.9300 | C32—C33 | 1.519 (5) |
C5—C6 | 1.386 (5) | C32—H32 | 0.9800 |
C5—H5 | 0.9300 | C33—C35 | 1.537 (5) |
C6—C7 | 1.470 (5) | C33—H33 | 0.9800 |
C7—C14 | 1.416 (5) | C34—C39 | 1.506 (5) |
C8—C13 | 1.398 (5) | C34—C38 | 1.516 (5) |
C8—C9 | 1.409 (5) | C35—H35 | 0.9800 |
C9—C10 | 1.356 (6) | C36—H36A | 0.9600 |
C9—H9 | 0.9300 | C36—H36B | 0.9600 |
C10—C11 | 1.396 (7) | C36—H36C | 0.9600 |
C10—H10 | 0.9300 | C37—H37A | 0.9600 |
C11—C12 | 1.364 (6) | C37—H37B | 0.9600 |
C11—H11 | 0.9300 | C37—H37C | 0.9600 |
C12—C13 | 1.408 (5) | C38—H38A | 0.9600 |
C12—H12 | 0.9300 | C38—H38B | 0.9600 |
C14—C15 | 1.530 (4) | C38—H38C | 0.9600 |
C15—C28 | 1.547 (4) | C39—H39A | 0.9600 |
C16—C17 | 1.511 (5) | C39—H39B | 0.9600 |
C16—H16A | 0.9700 | C39—H39C | 0.9600 |
C16—H16B | 0.9700 | ||
C22—O1—C21 | 114.7 (2) | C29—C21—C20 | 119.5 (2) |
C30—O4—C29 | 112.3 (2) | O1—C21—H21 | 107.4 |
C30—O5—C31 | 110.5 (3) | C29—C21—H21 | 107.4 |
C32—O6—C31 | 106.5 (3) | C20—C21—H21 | 107.4 |
C34—O7—C33 | 107.7 (3) | O1—C22—C27 | 121.5 (3) |
C34—O8—C35 | 107.5 (3) | O1—C22—C23 | 116.2 (3) |
C7—N1—C8 | 113.4 (3) | C27—C22—C23 | 122.2 (3) |
C14—N2—C13 | 114.1 (3) | C24—C23—C22 | 119.2 (4) |
C15—N3—C19 | 107.5 (2) | C24—C23—H23 | 120.4 |
C15—N3—C16 | 119.6 (2) | C22—C23—H23 | 120.4 |
C19—N3—C16 | 107.6 (3) | C23—C24—C25 | 120.4 (3) |
O2—N4—O3 | 123.4 (3) | C23—C24—H24 | 119.8 |
O2—N4—C20 | 119.7 (3) | C25—C24—H24 | 119.8 |
O3—N4—C20 | 116.9 (3) | C26—C25—C24 | 120.0 (4) |
C6—C1—C2 | 119.4 (3) | C26—C25—H25 | 120.0 |
C6—C1—C15 | 112.6 (3) | C24—C25—H25 | 120.0 |
C2—C1—C15 | 127.7 (3) | C25—C26—C27 | 120.7 (4) |
C3—C2—C1 | 118.1 (4) | C25—C26—H26 | 119.7 |
C3—C2—H2 | 120.9 | C27—C26—H26 | 119.7 |
C1—C2—H2 | 120.9 | C22—C27—C26 | 117.6 (3) |
C4—C3—C2 | 122.3 (4) | C22—C27—C28 | 121.0 (3) |
C4—C3—H3 | 118.8 | C26—C27—C28 | 121.3 (3) |
C2—C3—H3 | 118.8 | C27—C28—C15 | 116.9 (3) |
C3—C4—C5 | 120.1 (4) | C27—C28—C20 | 114.7 (3) |
C3—C4—H4 | 120.0 | C15—C28—C20 | 105.5 (2) |
C5—C4—H4 | 120.0 | C27—C28—H28 | 106.3 |
C6—C5—C4 | 118.0 (4) | C15—C28—H28 | 106.3 |
C6—C5—H5 | 121.0 | C20—C28—H28 | 106.3 |
C4—C5—H5 | 121.0 | O4—C29—C21 | 109.8 (2) |
C1—C6—C5 | 122.0 (3) | O4—C29—C35 | 108.4 (2) |
C1—C6—C7 | 108.5 (3) | C21—C29—C35 | 111.3 (3) |
C5—C6—C7 | 129.4 (4) | O4—C29—H29 | 109.1 |
N1—C7—C14 | 124.2 (3) | C21—C29—H29 | 109.1 |
N1—C7—C6 | 127.8 (3) | C35—C29—H29 | 109.1 |
C14—C7—C6 | 107.9 (3) | O4—C30—O5 | 111.1 (3) |
N1—C8—C13 | 122.3 (3) | O4—C30—C32 | 116.0 (3) |
N1—C8—C9 | 118.3 (4) | O5—C30—C32 | 103.9 (3) |
C13—C8—C9 | 119.4 (4) | O4—C30—H30 | 108.5 |
C10—C9—C8 | 119.6 (5) | O5—C30—H30 | 108.5 |
C10—C9—H9 | 120.2 | C32—C30—H30 | 108.5 |
C8—C9—H9 | 120.2 | O6—C31—O5 | 104.2 (3) |
C9—C10—C11 | 121.3 (4) | O6—C31—C36 | 108.6 (3) |
C9—C10—H10 | 119.4 | O5—C31—C36 | 109.2 (3) |
C11—C10—H10 | 119.4 | O6—C31—C37 | 110.9 (3) |
C12—C11—C10 | 120.4 (4) | O5—C31—C37 | 109.2 (3) |
C12—C11—H11 | 119.8 | C36—C31—C37 | 114.2 (4) |
C10—C11—H11 | 119.8 | O6—C32—C33 | 107.3 (3) |
C11—C12—C13 | 119.5 (5) | O6—C32—C30 | 103.6 (3) |
C11—C12—H12 | 120.2 | C33—C32—C30 | 115.3 (3) |
C13—C12—H12 | 120.2 | O6—C32—H32 | 110.1 |
N2—C13—C8 | 122.2 (3) | C33—C32—H32 | 110.1 |
N2—C13—C12 | 117.9 (4) | C30—C32—H32 | 110.1 |
C8—C13—C12 | 119.8 (4) | O7—C33—C32 | 107.6 (3) |
N2—C14—C7 | 123.7 (3) | O7—C33—C35 | 104.3 (3) |
N2—C14—C15 | 125.0 (3) | C32—C33—C35 | 115.0 (3) |
C7—C14—C15 | 111.3 (3) | O7—C33—H33 | 109.9 |
N3—C15—C14 | 107.8 (2) | C32—C33—H33 | 109.9 |
N3—C15—C1 | 115.0 (3) | C35—C33—H33 | 109.9 |
C14—C15—C1 | 99.6 (3) | O8—C34—O7 | 105.4 (3) |
N3—C15—C28 | 105.4 (3) | O8—C34—C39 | 108.9 (3) |
C14—C15—C28 | 114.9 (3) | O7—C34—C39 | 107.6 (3) |
C1—C15—C28 | 114.2 (2) | O8—C34—C38 | 110.6 (3) |
N3—C16—C17 | 101.1 (3) | O7—C34—C38 | 111.6 (3) |
N3—C16—H16A | 111.5 | C39—C34—C38 | 112.5 (4) |
C17—C16—H16A | 111.5 | O8—C35—C29 | 109.7 (3) |
N3—C16—H16B | 111.5 | O8—C35—C33 | 104.5 (2) |
C17—C16—H16B | 111.5 | C29—C35—C33 | 111.9 (3) |
H16A—C16—H16B | 109.4 | O8—C35—H35 | 110.2 |
C16—C17—C18 | 105.4 (3) | C29—C35—H35 | 110.2 |
C16—C17—H17A | 110.7 | C33—C35—H35 | 110.2 |
C18—C17—H17A | 110.7 | C31—C36—H36A | 109.5 |
C16—C17—H17B | 110.7 | C31—C36—H36B | 109.5 |
C18—C17—H17B | 110.7 | H36A—C36—H36B | 109.5 |
H17A—C17—H17B | 108.8 | C31—C36—H36C | 109.5 |
C17—C18—C19 | 104.9 (3) | H36A—C36—H36C | 109.5 |
C17—C18—H18A | 110.8 | H36B—C36—H36C | 109.5 |
C19—C18—H18A | 110.8 | C31—C37—H37A | 109.5 |
C17—C18—H18B | 110.8 | C31—C37—H37B | 109.5 |
C19—C18—H18B | 110.8 | H37A—C37—H37B | 109.5 |
H18A—C18—H18B | 108.8 | C31—C37—H37C | 109.5 |
N3—C19—C18 | 105.2 (3) | H37A—C37—H37C | 109.5 |
N3—C19—C20 | 106.9 (2) | H37B—C37—H37C | 109.5 |
C18—C19—C20 | 121.0 (3) | C34—C38—H38A | 109.5 |
N3—C19—H19 | 107.7 | C34—C38—H38B | 109.5 |
C18—C19—H19 | 107.7 | H38A—C38—H38B | 109.5 |
C20—C19—H19 | 107.7 | C34—C38—H38C | 109.5 |
N4—C20—C21 | 111.8 (3) | H38A—C38—H38C | 109.5 |
N4—C20—C28 | 107.6 (2) | H38B—C38—H38C | 109.5 |
C21—C20—C28 | 110.8 (2) | C34—C39—H39A | 109.5 |
N4—C20—C19 | 111.2 (2) | C34—C39—H39B | 109.5 |
C21—C20—C19 | 110.5 (2) | H39A—C39—H39B | 109.5 |
C28—C20—C19 | 104.7 (2) | C34—C39—H39C | 109.5 |
O1—C21—C29 | 103.4 (2) | H39A—C39—H39C | 109.5 |
O1—C21—C20 | 111.3 (2) | H39B—C39—H39C | 109.5 |
C6—C1—C2—C3 | −1.2 (5) | N4—C20—C21—O1 | 68.0 (3) |
C15—C1—C2—C3 | −174.9 (3) | C28—C20—C21—O1 | −52.0 (3) |
C1—C2—C3—C4 | −0.4 (6) | C19—C20—C21—O1 | −167.5 (2) |
C2—C3—C4—C5 | 1.6 (6) | N4—C20—C21—C29 | −52.3 (3) |
C3—C4—C5—C6 | −1.1 (6) | C28—C20—C21—C29 | −172.3 (3) |
C2—C1—C6—C5 | 1.6 (5) | C19—C20—C21—C29 | 72.1 (3) |
C15—C1—C6—C5 | 176.2 (3) | C21—O1—C22—C27 | −31.8 (4) |
C2—C1—C6—C7 | −174.6 (3) | C21—O1—C22—C23 | 151.3 (3) |
C15—C1—C6—C7 | 0.0 (4) | O1—C22—C23—C24 | 177.6 (3) |
C4—C5—C6—C1 | −0.4 (5) | C27—C22—C23—C24 | 0.7 (5) |
C4—C5—C6—C7 | 174.9 (3) | C22—C23—C24—C25 | −0.5 (6) |
C8—N1—C7—C14 | 0.1 (4) | C23—C24—C25—C26 | −0.2 (6) |
C8—N1—C7—C6 | −177.3 (3) | C24—C25—C26—C27 | 0.9 (6) |
C1—C6—C7—N1 | 179.6 (3) | O1—C22—C27—C26 | −176.8 (3) |
C5—C6—C7—N1 | 3.8 (6) | C23—C22—C27—C26 | 0.0 (5) |
C1—C6—C7—C14 | 1.8 (4) | O1—C22—C27—C28 | −0.3 (5) |
C5—C6—C7—C14 | −174.0 (3) | C23—C22—C27—C28 | 176.5 (3) |
C7—N1—C8—C13 | −0.2 (5) | C25—C26—C27—C22 | −0.7 (5) |
C7—N1—C8—C9 | 178.9 (3) | C25—C26—C27—C28 | −177.2 (3) |
N1—C8—C9—C10 | 179.5 (4) | C22—C27—C28—C15 | 128.1 (3) |
C13—C8—C9—C10 | −1.4 (6) | C26—C27—C28—C15 | −55.5 (4) |
C8—C9—C10—C11 | 1.4 (7) | C22—C27—C28—C20 | 3.8 (4) |
C9—C10—C11—C12 | −0.5 (8) | C26—C27—C28—C20 | −179.8 (3) |
C10—C11—C12—C13 | −0.4 (8) | N3—C15—C28—C27 | −155.5 (3) |
C14—N2—C13—C8 | 0.6 (5) | C14—C15—C28—C27 | −36.9 (4) |
C14—N2—C13—C12 | −179.1 (3) | C1—C15—C28—C27 | 77.4 (3) |
N1—C8—C13—N2 | −0.2 (5) | N3—C15—C28—C20 | −26.6 (3) |
C9—C8—C13—N2 | −179.2 (3) | C14—C15—C28—C20 | 91.9 (3) |
N1—C8—C13—C12 | 179.5 (3) | C1—C15—C28—C20 | −153.8 (3) |
C9—C8—C13—C12 | 0.5 (5) | N4—C20—C28—C27 | −100.7 (3) |
C11—C12—C13—N2 | −179.8 (4) | C21—C20—C28—C27 | 21.8 (3) |
C11—C12—C13—C8 | 0.4 (6) | C19—C20—C28—C27 | 140.9 (3) |
C13—N2—C14—C7 | −0.7 (5) | N4—C20—C28—C15 | 129.2 (3) |
C13—N2—C14—C15 | −179.3 (3) | C21—C20—C28—C15 | −108.3 (3) |
N1—C7—C14—N2 | 0.3 (5) | C19—C20—C28—C15 | 10.8 (3) |
C6—C7—C14—N2 | 178.2 (3) | C30—O4—C29—C21 | 165.9 (3) |
N1—C7—C14—C15 | 179.1 (3) | C30—O4—C29—C35 | −72.3 (3) |
C6—C7—C14—C15 | −3.0 (4) | O1—C21—C29—O4 | −160.0 (2) |
C19—N3—C15—C14 | −90.3 (3) | C20—C21—C29—O4 | −35.7 (4) |
C16—N3—C15—C14 | 146.7 (3) | O1—C21—C29—C35 | 80.0 (3) |
C19—N3—C15—C1 | 159.6 (3) | C20—C21—C29—C35 | −155.7 (3) |
C16—N3—C15—C1 | 36.6 (4) | C29—O4—C30—O5 | −80.2 (3) |
C19—N3—C15—C28 | 32.9 (3) | C29—O4—C30—C32 | 38.1 (4) |
C16—N3—C15—C28 | −90.1 (3) | C31—O5—C30—O4 | 126.4 (3) |
N2—C14—C15—N3 | 61.3 (4) | C31—O5—C30—C32 | 0.9 (4) |
C7—C14—C15—N3 | −117.5 (3) | C32—O6—C31—O5 | 33.2 (4) |
N2—C14—C15—C1 | −178.4 (3) | C32—O6—C31—C36 | 149.5 (3) |
C7—C14—C15—C1 | 2.8 (3) | C32—O6—C31—C37 | −84.2 (4) |
N2—C14—C15—C28 | −55.9 (4) | C30—O5—C31—O6 | −20.6 (4) |
C7—C14—C15—C28 | 125.4 (3) | C30—O5—C31—C36 | −136.5 (3) |
C6—C1—C15—N3 | 113.3 (3) | C30—O5—C31—C37 | 98.0 (4) |
C2—C1—C15—N3 | −72.6 (4) | C31—O6—C32—C33 | −154.8 (3) |
C6—C1—C15—C14 | −1.7 (3) | C31—O6—C32—C30 | −32.4 (3) |
C2—C1—C15—C14 | 172.4 (3) | O4—C30—C32—O6 | −103.1 (3) |
C6—C1—C15—C28 | −124.7 (3) | O5—C30—C32—O6 | 19.1 (3) |
C2—C1—C15—C28 | 49.4 (4) | O4—C30—C32—C33 | 13.9 (4) |
C15—N3—C16—C17 | 162.1 (3) | O5—C30—C32—C33 | 136.1 (3) |
C19—N3—C16—C17 | 39.1 (3) | C34—O7—C33—C32 | −142.0 (3) |
N3—C16—C17—C18 | −37.0 (3) | C34—O7—C33—C35 | −19.4 (3) |
C16—C17—C18—C19 | 22.1 (4) | O6—C32—C33—O7 | −160.4 (3) |
C15—N3—C19—C18 | −155.9 (2) | C30—C32—C33—O7 | 84.7 (4) |
C16—N3—C19—C18 | −25.8 (3) | O6—C32—C33—C35 | 83.9 (4) |
C15—N3—C19—C20 | −26.1 (3) | C30—C32—C33—C35 | −31.0 (4) |
C16—N3—C19—C20 | 104.1 (3) | C35—O8—C34—O7 | −31.9 (3) |
C17—C18—C19—N3 | 1.7 (3) | C35—O8—C34—C39 | −147.1 (3) |
C17—C18—C19—C20 | −119.3 (3) | C35—O8—C34—C38 | 88.8 (4) |
O2—N4—C20—C21 | 6.9 (4) | C33—O7—C34—O8 | 32.1 (3) |
O3—N4—C20—C21 | −173.4 (3) | C33—O7—C34—C39 | 148.2 (3) |
O2—N4—C20—C28 | 128.7 (3) | C33—O7—C34—C38 | −88.0 (3) |
O3—N4—C20—C28 | −51.6 (4) | C34—O8—C35—C29 | 139.5 (3) |
O2—N4—C20—C19 | −117.2 (3) | C34—O8—C35—C33 | 19.3 (3) |
O3—N4—C20—C19 | 62.5 (4) | O4—C29—C35—O8 | −64.6 (3) |
N3—C19—C20—N4 | −107.3 (3) | C21—C29—C35—O8 | 56.2 (3) |
C18—C19—C20—N4 | 12.9 (4) | O4—C29—C35—C33 | 50.9 (4) |
N3—C19—C20—C21 | 128.0 (3) | C21—C29—C35—C33 | 171.7 (2) |
C18—C19—C20—C21 | −111.9 (3) | O7—C33—C35—O8 | 0.1 (3) |
N3—C19—C20—C28 | 8.6 (3) | C32—C33—C35—O8 | 117.7 (3) |
C18—C19—C20—C28 | 128.8 (3) | O7—C33—C35—C29 | −118.6 (3) |
C22—O1—C21—C29 | −172.3 (2) | C32—C33—C35—C29 | −1.0 (4) |
C22—O1—C21—C20 | 58.3 (3) |
Cg8 is the centroid of the N1/C7/C14/N2/C13/C8 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C35—H35···O2i | 0.98 | 2.41 | 3.390 (4) | 177 |
C16—H16A···O3 | 0.97 | 2.59 | 3.237 (5) | 124 |
C21—H21···N2 | 0.98 | 2.48 | 3.305 (4) | 141 |
C30—H30···Cg8ii | 0.98 | 2.93 | 3.895 (4) | 168 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x, y−1/2, −z+1/2. |
Cg8 is the centroid of the N1/C7/C14/N2/C13/C8 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C35—H35···O2i | 0.98 | 2.41 | 3.390 (4) | 177.0 |
C16—H16A···O3 | 0.97 | 2.59 | 3.237 (5) | 124.0 |
C21—H21···N2 | 0.98 | 2.48 | 3.305 (4) | 141.4 |
C30—H30···Cg8ii | 0.98 | 2.93 | 3.895 (4) | 168 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x, y−1/2, −z+1/2. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.
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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.
Spiro compounds are a particular class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). Quinoxaline derivatives are an important class of benzoheterocycles. They have found applications as anticancer, antiviral, and antibacterial agents (Seitz et al., 2002; He et al., 2003).
In the title compound, C39H38N4O8, the quinoxaline (C7—C14\N1\N2) and indene (C1—C7\C14\C15) subunits are essentially planar with maximum deviations of -0.071 (2) Å for C14 and -0.009 (1) Å for C9, respectively. The dihedral angle between the chromeno-pyrrolizine (C15—C28\N2\N3\O1) and indeno-quinoxaline (C—C15\N1\N2) systems is 72.81 (3)° showing their almost orthogonal arrangement relative to each other.
The two dioxolane rings (C30—C32\O5\O6,C33—C35\O7\O8) which are fused with a pyran ring adopt an envelope conformation with O6 and C34 atoms as the flap. Puckering parameters are q2 = 0.3089 (1) Å, Φ2 = 108.05 (2)° and q2 = 0.2905 (1) Å, Φ2 = 324.14 (2)°, respectively. The pyran ring (C20—C22\C27\C28\O1) of the chromeno group and the pyrrolizine ring (C16—C19\N3) also adopt envelope conformations with O1 and C16 atoms as the flap. Puckering parameters are q2 = 0.3895 (1) Å, q3 = -0.2566 Å, Φ2 = 235.74 (2)°, Θ = 123.38° for the pyran and q2 = 0.3781 (1) Å, Φ2 = 213.99 (4)° for the pyrrolizine system, respectively. The pyrrolizine ring fused with the pyran ring adopts a twisted conformation along N3—C15 with puckering parameters of q2 = 0.301 (1) Å, Φ2 = 200.75 (2)° (Cremer & Pople, 1975).
The structure is stabilized by an intermolecular C—H···O hydrogen bond and additional intramolecular C—H···O and C—H···N hydrogen bonds (Table 1). The crystal structure is further consolidated by C—H ···Cg8 interactions where Cg8 is the centroid of C7\C8\C13\C14\N1\N2 ring.