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]

Anuradha, T.; Naga Siva Rao, J.; Seshadri, P.R.; Raghunathan, R.

doi:10.1107/S1600536813032467

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 1| January 2014| Pages o38-o39

https://doi.org/10.1107/S1600536813032467

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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]

T. Anuradha,^a J. Naga Siva Rao,^b P. R. Seshadri ^a ^* and R. Raghunathan ^b

^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

(Received 18 September 2013; accepted 28 November 2013; online 14 December 2013)

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 envelope conformation 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 crystal structure 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 spiro compounds 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 ).

Experimental

Crystal data

C₃₉H₃₈N₄O₈
M_r = 690.73
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.3150 (9) Å
b = 15.629 (2) Å
c = 19.419 (2) Å
V = 3434.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.981, T_max = 0.991
15819 measured reflections
6671 independent reflections
3789 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.124
S = 0.97
6671 reflections
460 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 2933 Friedel pairs
Absolute structure parameter: 0.30 (13)

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: 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

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536813032467/im2440sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032467/im2440Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For some spiro compounds 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).

Experimental top

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 column chromatography using hexane/EtOAc (7:3) as eluent (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.

Structure description top

For some spiro compounds 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).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: 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).

Figures top

	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).

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] top

Crystal data top

C₃₉H₃₈N₄O₈	F(000) = 1456
M_r = 690.73	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	6671 independent reflections
Radiation source: fine-focus sealed tube	3789 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω and φ scan	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
T_min = 0.981, T_max = 0.991	k = −19→18
15819 measured reflections	l = −23→23

Refinement top

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(F_o²) + (0.047P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
6671 reflections	Δρ_max = 0.17 e Å⁻³
460 parameters	Δρ_min = −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)

Crystal data top

C₃₉H₃₈N₄O₈	V = 3434.0 (6) Å³
M_r = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	6671 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3789 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.991	R_int = 0.059
15819 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.124	Δρ_max = 0.17 e Å⁻³
S = 0.97	Δρ_min = −0.20 e Å⁻³
6671 reflections	Absolute structure: Flack (1983), 2933 Friedel pairs
460 parameters	Absolute structure parameter: 0.30 (13)
0 restraints

Special details top

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

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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.

References

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Volume 70| Part 1| January 2014| Pages o38-o39

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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]