6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octa­hydro­spiro­[chromeno[3,4-a]indol­izine-12,3′-indolin]-2′-one

Devi, S.K.; Srinivasan, T.; Rao, J.N.S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536813014062

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o993

doi:10.1107/S1600536813014062

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6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octahydrospiro[chromeno[3,4-a]indolizine-12,3′-indolin]-2′-one

Seenivasan Karthiga Devi,^a Thothadri Srinivasan,^a Jonnalagadda Naga Siva Rao,^b Raghavachary Raghunathan ^b and Devadasan Velmurugan ^a ^*

^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

(Received 18 May 2013; accepted 21 May 2013; online 31 May 2013)

In the title compound, C₂₈H₂₅N₃O₄, the central pyrrolidine ring adopts adopts an envelope conformation with the N atom as the flap and the piperidine ring adopts a chair conformation. The pendant pyrrolidine ring is almost planar (r.m.s. deviation = 0.008 Å). An intramolecular C—H⋯O interaction closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops.

Related literature

For biological background to 4H-chromene derivatives, see: Cai (2008 ); Valenti et al. (1993 ). For applications of indoline-2-one and its derivatives as precursors in the synthesis of pharmaceuticals, see: Colgan et al. (1996 ).

Experimental

Crystal data

C₂₈H₂₅N₃O₄
M_r = 467.51
Monoclinic, C 2/c
a = 23.2940 (13) Å
b = 11.2517 (7) Å
c = 19.7702 (10) Å
β = 112.659 (3)°
V = 4781.8 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.974, T_max = 0.983
20735 measured reflections
5804 independent reflections
3892 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.127
S = 1.00
5804 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O4	0.98	2.50	3.1394 (18)	123
N3—H3A⋯O4ⁱ	0.86	1.97	2.8218 (17)	168
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813014062/hb7084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813014062/hb7084Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813014062/hb7084Isup3.cml

checkCIF report

Comment top

4H-Chromenes are biologically important compounds used in the drug-discovery process (e.g. Valenti et al., 1993; Cai, 2008). Indoline-2-one and its derivatives have been used as precursors to synthesis pharmaceuticals (Colgan et al., 1996). Continuing our interest in such compounds we have synthesized the title compound and report herein its crystal structure.

In the title compound, C₂₈H₂₅N₃O₄, (fig.1) the pyrrolidine ring adopts an envelope conformation and the piperidine ring adopts a chair conformation. The pyrrolidine ring (N2/C7/C8/C16/C21) makes a dihedral angle of 84.13 (9)° with the other pyrrolidine ring (N3/C21/C22/C27/C28) which shows that they are almost orthogonal to each other. The pyrrolidine ring makes a dihedral angle of 61.22 (8)° with the the pyran ring (O1/C1/C6-C9), it makes a dihedral angle of 4.00 (9)° with the piperidine ring (N2/C16-C20).

The other pyrrolidine ring (N3/C21/C22/C27/C28) makes a dihedral angle of 39.60 (9)° with the pyran ring, it makes a dihedral angle of 88.12 (9)° with the piperidine ring which shows that they are almost at right angles to each other. The dihedral angle between the pyran ring and the piperidine ring is 57.58 (9)° . The oxygen atom O4 attached with pyrrolidine ring deviates by -0.0736 (1)Å. The nitrogroup attached with the pyrrolidine ring makes a diherdal angle of 88.81 (2)° which shows it is in orthogonal orientation . The crystal packing features N—H···O hydrogen bonds and an intramolecular C—H···O hydrogen bond is also observed.

Related literature top

For biological background to 4H-chromene derivatives, see: Cai (2008); Valenti et al. (1993). For applications of indoline-2-one and its derivatives as precursors in the synthesis of pharmaceuticals, see: Colgan et al. (1996).

Experimental top

To a solution of isatin (1 equiv) and piperidine-2-carboxylic acid (1.4 equiv) in dry toluene, was added 3-nitro-2-phenyl-2H-chromene (1equiv) under nitrogen atmosphere. The reaction mixture was refluxed f or 24h in Dean-Stark apparatus to give the cycloadducts. 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 sulphate and concentrated in vacuo. Then the crude product was purified by column chromatography using hexane/EtOAc (7:3) as eluent. Colourless blocks were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. An inversion dimer in the crystal of the title compound viewed down [100].

6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octahydrospiro[chromeno[3,4-a]indolizine-12,3'-indolin]-2'-one top

Crystal data top

C₂₈H₂₅N₃O₄	F(000) = 1968
M_r = 467.51	D_x = 1.299 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5804 reflections
a = 23.2940 (13) Å	θ = 1.9–28.3°
b = 11.2517 (7) Å	µ = 0.09 mm⁻¹
c = 19.7702 (10) Å	T = 293 K
β = 112.659 (3)°	Block, colourless
V = 4781.8 (5) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	5804 independent reflections
Radiation source: fine-focus sealed tube	3892 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω and ϕ scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −30→27
T_min = 0.974, T_max = 0.983	k = −14→14
20735 measured reflections	l = −25→25

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0505P)² + 2.441P] where P = (F_o² + 2F_c²)/3
5804 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₈H₂₅N₃O₄	V = 4781.8 (5) Å³
M_r = 467.51	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.2940 (13) Å	µ = 0.09 mm⁻¹
b = 11.2517 (7) Å	T = 293 K
c = 19.7702 (10) Å	0.30 × 0.25 × 0.20 mm
β = 112.659 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5804 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3892 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.983	R_int = 0.048
20735 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.00	Δρ_max = 0.22 e Å⁻³
5804 reflections	Δρ_min = −0.22 e Å⁻³
316 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.85609 (7)	−0.07457 (14)	0.50076 (8)	0.0424 (4)
C2	0.86024 (10)	−0.05264 (18)	0.43391 (10)	0.0608 (5)
H2	0.8376	−0.0985	0.3932	0.073*
C3	0.89794 (11)	0.0370 (2)	0.42802 (12)	0.0740 (6)
H3	0.8998	0.0536	0.3828	0.089*
C4	0.93302 (11)	0.1027 (2)	0.48873 (12)	0.0725 (6)
H4	0.9592	0.1624	0.4848	0.087*
C5	0.92917 (8)	0.07964 (16)	0.55536 (10)	0.0530 (4)
H5	0.9531	0.1237	0.5963	0.064*
C6	0.89013 (7)	−0.00828 (13)	0.56210 (8)	0.0384 (3)
C7	0.88197 (6)	−0.02739 (12)	0.63324 (7)	0.0333 (3)
H7	0.9232	−0.0262	0.6731	0.040*
C8	0.85040 (7)	−0.14626 (12)	0.63696 (7)	0.0337 (3)
C9	0.83905 (7)	−0.23119 (13)	0.57169 (8)	0.0383 (3)
H9	0.8051	−0.2843	0.5699	0.046*
C10	0.89189 (7)	−0.30987 (14)	0.57303 (8)	0.0399 (4)
C11	0.95412 (8)	−0.27872 (16)	0.60526 (10)	0.0514 (4)
H11	0.9652	−0.2047	0.6274	0.062*
C12	0.99985 (9)	−0.35599 (18)	0.60498 (10)	0.0592 (5)
H12	1.0415	−0.3343	0.6271	0.071*
C13	0.98385 (11)	−0.46543 (19)	0.57194 (10)	0.0629 (5)
H13	1.0147	−0.5178	0.5718	0.075*
C14	0.92229 (11)	−0.49735 (17)	0.53910 (11)	0.0660 (6)
H14	0.9115	−0.5711	0.5165	0.079*
C15	0.87660 (9)	−0.42018 (15)	0.53967 (9)	0.0505 (4)
H15	0.8350	−0.4423	0.5174	0.061*
C16	0.78884 (7)	−0.11043 (13)	0.64328 (8)	0.0364 (3)
H16	0.7581	−0.0947	0.5938	0.044*
C17	0.75963 (8)	−0.19292 (15)	0.68128 (10)	0.0490 (4)
H17A	0.7892	−0.2104	0.7304	0.059*
H17B	0.7481	−0.2671	0.6544	0.059*
C18	0.70199 (9)	−0.13326 (17)	0.68491 (11)	0.0585 (5)
H18A	0.6715	−0.1204	0.6357	0.070*
H18B	0.6836	−0.1846	0.7105	0.070*
C19	0.71962 (9)	−0.01512 (18)	0.72468 (12)	0.0624 (5)
H19A	0.6825	0.0240	0.7248	0.075*
H19B	0.7474	−0.0288	0.7752	0.075*
C20	0.75132 (8)	0.06411 (15)	0.68767 (11)	0.0535 (4)
H20A	0.7221	0.0850	0.6390	0.064*
H20B	0.7650	0.1369	0.7156	0.064*
C21	0.84106 (6)	0.07028 (12)	0.64953 (7)	0.0335 (3)
C22	0.87723 (7)	0.17155 (12)	0.69677 (8)	0.0339 (3)
C23	0.92160 (7)	0.17261 (14)	0.76717 (8)	0.0420 (4)
H23	0.9341	0.1023	0.7935	0.050*
C24	0.94731 (8)	0.28065 (15)	0.79802 (9)	0.0476 (4)
H24	0.9772	0.2829	0.8456	0.057*
C25	0.92886 (8)	0.38464 (15)	0.75866 (9)	0.0460 (4)
H25	0.9469	0.4561	0.7801	0.055*
C26	0.88421 (7)	0.38502 (14)	0.68819 (9)	0.0422 (4)
H26	0.8716	0.4554	0.6619	0.051*
C27	0.85910 (7)	0.27729 (13)	0.65836 (8)	0.0359 (3)
C28	0.79893 (7)	0.13765 (13)	0.57914 (8)	0.0372 (3)
N1	0.88825 (6)	−0.21232 (12)	0.70783 (7)	0.0411 (3)
N2	0.80488 (6)	0.00268 (11)	0.68254 (7)	0.0375 (3)
N3	0.81272 (6)	0.25411 (11)	0.58899 (7)	0.0435 (3)
H3A	0.7953	0.3079	0.5567	0.052*
O1	0.81579 (5)	−0.16138 (10)	0.50491 (5)	0.0439 (3)
O2	0.92442 (6)	−0.15660 (11)	0.75982 (6)	0.0606 (4)
O3	0.87676 (6)	−0.31771 (10)	0.70992 (6)	0.0546 (3)
O4	0.75833 (5)	0.09239 (9)	0.52555 (6)	0.0476 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0445 (9)	0.0376 (9)	0.0414 (8)	−0.0021 (7)	0.0124 (7)	0.0040 (7)
C2	0.0756 (13)	0.0620 (12)	0.0431 (9)	−0.0079 (10)	0.0209 (9)	−0.0001 (9)
C3	0.1009 (17)	0.0740 (14)	0.0602 (12)	−0.0132 (13)	0.0456 (12)	0.0058 (11)
C4	0.0894 (15)	0.0648 (14)	0.0804 (14)	−0.0232 (12)	0.0516 (13)	0.0011 (11)
C5	0.0565 (11)	0.0469 (10)	0.0600 (10)	−0.0152 (8)	0.0272 (9)	−0.0037 (8)
C6	0.0386 (8)	0.0327 (8)	0.0425 (8)	−0.0006 (6)	0.0141 (7)	0.0027 (6)
C7	0.0309 (7)	0.0269 (7)	0.0351 (7)	−0.0028 (6)	0.0050 (6)	0.0011 (6)
C8	0.0346 (7)	0.0267 (7)	0.0340 (7)	−0.0007 (6)	0.0067 (6)	0.0034 (6)
C9	0.0416 (8)	0.0291 (7)	0.0381 (8)	−0.0055 (6)	0.0085 (7)	0.0004 (6)
C10	0.0484 (9)	0.0334 (8)	0.0350 (7)	−0.0005 (7)	0.0130 (7)	−0.0001 (6)
C11	0.0492 (10)	0.0438 (10)	0.0557 (10)	0.0023 (8)	0.0142 (8)	−0.0056 (8)
C12	0.0548 (11)	0.0661 (13)	0.0552 (10)	0.0120 (10)	0.0195 (9)	0.0024 (9)
C13	0.0809 (14)	0.0625 (13)	0.0500 (10)	0.0290 (11)	0.0305 (10)	0.0065 (9)
C14	0.1004 (17)	0.0413 (10)	0.0585 (11)	0.0087 (11)	0.0328 (12)	−0.0093 (9)
C15	0.0646 (11)	0.0389 (9)	0.0447 (9)	−0.0042 (8)	0.0175 (8)	−0.0054 (7)
C16	0.0354 (8)	0.0300 (8)	0.0397 (8)	−0.0029 (6)	0.0101 (6)	0.0021 (6)
C17	0.0516 (10)	0.0371 (9)	0.0606 (10)	−0.0074 (8)	0.0241 (9)	0.0033 (8)
C18	0.0541 (11)	0.0533 (11)	0.0776 (13)	−0.0084 (9)	0.0360 (10)	0.0040 (10)
C19	0.0634 (12)	0.0560 (12)	0.0832 (13)	−0.0019 (10)	0.0452 (11)	−0.0041 (10)
C20	0.0532 (10)	0.0387 (10)	0.0753 (12)	0.0009 (8)	0.0319 (9)	−0.0037 (8)
C21	0.0341 (7)	0.0262 (7)	0.0345 (7)	−0.0002 (6)	0.0068 (6)	0.0029 (6)
C22	0.0345 (7)	0.0273 (7)	0.0379 (7)	−0.0009 (6)	0.0117 (6)	−0.0001 (6)
C23	0.0423 (9)	0.0351 (8)	0.0399 (8)	0.0034 (7)	0.0063 (7)	0.0011 (6)
C24	0.0427 (9)	0.0447 (10)	0.0441 (9)	0.0005 (8)	0.0041 (7)	−0.0085 (7)
C25	0.0460 (9)	0.0358 (9)	0.0540 (9)	−0.0071 (7)	0.0167 (8)	−0.0114 (7)
C26	0.0504 (9)	0.0266 (8)	0.0491 (9)	−0.0019 (7)	0.0186 (8)	0.0004 (6)
C27	0.0371 (8)	0.0299 (8)	0.0377 (7)	−0.0014 (6)	0.0110 (6)	0.0011 (6)
C28	0.0361 (8)	0.0306 (8)	0.0394 (8)	0.0009 (6)	0.0085 (6)	0.0033 (6)
N1	0.0458 (7)	0.0324 (7)	0.0415 (7)	0.0043 (6)	0.0126 (6)	0.0043 (5)
N2	0.0387 (7)	0.0285 (6)	0.0452 (7)	−0.0016 (5)	0.0159 (6)	0.0010 (5)
N3	0.0499 (8)	0.0264 (7)	0.0408 (7)	0.0003 (6)	0.0026 (6)	0.0066 (5)
O1	0.0446 (6)	0.0399 (6)	0.0360 (5)	−0.0074 (5)	0.0030 (5)	0.0022 (4)
O2	0.0669 (8)	0.0510 (7)	0.0413 (6)	−0.0021 (6)	−0.0040 (6)	0.0037 (6)
O3	0.0733 (8)	0.0299 (6)	0.0580 (7)	0.0041 (6)	0.0225 (6)	0.0117 (5)
O4	0.0451 (6)	0.0350 (6)	0.0431 (6)	−0.0030 (5)	−0.0045 (5)	0.0032 (5)

Geometric parameters (Å, º) top

C1—O1	1.3790 (19)	C16—C17	1.511 (2)
C1—C6	1.384 (2)	C16—H16	0.9800
C1—C2	1.384 (2)	C17—C18	1.527 (2)
C2—C3	1.372 (3)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.378 (3)	C18—C19	1.518 (3)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.379 (3)	C18—H18B	0.9700
C4—H4	0.9300	C19—C20	1.514 (3)
C5—C6	1.385 (2)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C6—C7	1.505 (2)	C20—N2	1.464 (2)
C7—C8	1.5417 (19)	C20—H20A	0.9700
C7—C21	1.567 (2)	C20—H20B	0.9700
C7—H7	0.9800	C21—N2	1.4624 (18)
C8—N1	1.5301 (18)	C21—C22	1.5080 (19)
C8—C16	1.540 (2)	C21—C28	1.5563 (19)
C8—C9	1.544 (2)	C22—C23	1.377 (2)
C9—O1	1.4499 (17)	C22—C27	1.387 (2)
C9—C10	1.508 (2)	C23—C24	1.388 (2)
C9—H9	0.9800	C23—H23	0.9300
C10—C11	1.385 (2)	C24—C25	1.379 (2)
C10—C15	1.386 (2)	C24—H24	0.9300
C11—C12	1.377 (2)	C25—C26	1.381 (2)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.376 (3)	C26—C27	1.376 (2)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.375 (3)	C27—N3	1.4050 (19)
C13—H13	0.9300	C28—O4	1.2264 (17)
C14—C15	1.377 (3)	C28—N3	1.3454 (19)
C14—H14	0.9300	N1—O3	1.2199 (17)
C15—H15	0.9300	N1—O2	1.2216 (17)
C16—N2	1.4623 (18)	N3—H3A	0.8600

O1—C1—C6	120.19 (14)	C16—C17—H17A	109.9
O1—C1—C2	118.86 (15)	C18—C17—H17A	109.9
C6—C1—C2	120.91 (16)	C16—C17—H17B	109.9
C3—C2—C1	119.64 (18)	C18—C17—H17B	109.9
C3—C2—H2	120.2	H17A—C17—H17B	108.3
C1—C2—H2	120.2	C19—C18—C17	109.99 (15)
C2—C3—C4	120.33 (18)	C19—C18—H18A	109.7
C2—C3—H3	119.8	C17—C18—H18A	109.7
C4—C3—H3	119.8	C19—C18—H18B	109.7
C3—C4—C5	119.73 (18)	C17—C18—H18B	109.7
C3—C4—H4	120.1	H18A—C18—H18B	108.2
C5—C4—H4	120.1	C20—C19—C18	110.49 (15)
C4—C5—C6	120.89 (17)	C20—C19—H19A	109.6
C4—C5—H5	119.6	C18—C19—H19A	109.6
C6—C5—H5	119.6	C20—C19—H19B	109.6
C1—C6—C5	118.47 (15)	C18—C19—H19B	109.6
C1—C6—C7	120.39 (13)	H19A—C19—H19B	108.1
C5—C6—C7	121.06 (14)	N2—C20—C19	110.06 (14)
C6—C7—C8	113.75 (12)	N2—C20—H20A	109.6
C6—C7—C21	113.41 (11)	C19—C20—H20A	109.6
C8—C7—C21	105.04 (11)	N2—C20—H20B	109.6
C6—C7—H7	108.1	C19—C20—H20B	109.6
C8—C7—H7	108.1	H20A—C20—H20B	108.2
C21—C7—H7	108.1	N2—C21—C22	113.40 (12)
N1—C8—C16	106.20 (11)	N2—C21—C28	112.27 (11)
N1—C8—C7	110.35 (11)	C22—C21—C28	101.25 (11)
C16—C8—C7	104.66 (11)	N2—C21—C7	103.15 (11)
N1—C8—C9	108.50 (11)	C22—C21—C7	114.73 (11)
C16—C8—C9	111.39 (12)	C28—C21—C7	112.45 (11)
C7—C8—C9	115.35 (12)	C23—C22—C27	119.84 (13)
O1—C9—C10	110.48 (12)	C23—C22—C21	130.92 (13)
O1—C9—C8	108.02 (11)	C27—C22—C21	109.24 (12)
C10—C9—C8	118.21 (12)	C22—C23—C24	118.71 (14)
O1—C9—H9	106.5	C22—C23—H23	120.6
C10—C9—H9	106.5	C24—C23—H23	120.6
C8—C9—H9	106.5	C25—C24—C23	120.47 (14)
C11—C10—C15	118.49 (16)	C25—C24—H24	119.8
C11—C10—C9	124.19 (14)	C23—C24—H24	119.8
C15—C10—C9	117.32 (15)	C24—C25—C26	121.47 (15)
C12—C11—C10	120.83 (17)	C24—C25—H25	119.3
C12—C11—H11	119.6	C26—C25—H25	119.3
C10—C11—H11	119.6	C27—C26—C25	117.41 (14)
C13—C12—C11	119.90 (19)	C27—C26—H26	121.3
C13—C12—H12	120.0	C25—C26—H26	121.3
C11—C12—H12	120.0	C26—C27—C22	122.11 (14)
C14—C13—C12	120.03 (18)	C26—C27—N3	128.46 (14)
C14—C13—H13	120.0	C22—C27—N3	109.43 (12)
C12—C13—H13	120.0	O4—C28—N3	126.24 (14)
C13—C14—C15	120.03 (18)	O4—C28—C21	125.52 (13)
C13—C14—H14	120.0	N3—C28—C21	108.16 (12)
C15—C14—H14	120.0	O3—N1—O2	124.03 (13)
C14—C15—C10	120.72 (18)	O3—N1—C8	116.53 (12)
C14—C15—H15	119.6	O2—N1—C8	119.25 (12)
C10—C15—H15	119.6	C16—N2—C21	106.81 (11)
N2—C16—C17	110.04 (13)	C16—N2—C20	113.42 (12)
N2—C16—C8	102.43 (11)	C21—N2—C20	116.01 (12)
C17—C16—C8	119.42 (13)	C28—N3—C27	111.91 (12)
N2—C16—H16	108.1	C28—N3—H3A	124.0
C17—C16—H16	108.1	C27—N3—H3A	124.0
C8—C16—H16	108.1	C1—O1—C9	114.45 (11)
C16—C17—C18	109.01 (14)

O1—C1—C2—C3	177.03 (18)	C8—C7—C21—C22	140.86 (12)
C6—C1—C2—C3	−0.9 (3)	C6—C7—C21—C28	20.67 (16)
C1—C2—C3—C4	2.0 (3)	C8—C7—C21—C28	−104.13 (13)
C2—C3—C4—C5	−1.3 (4)	N2—C21—C22—C23	57.8 (2)
C3—C4—C5—C6	−0.5 (3)	C28—C21—C22—C23	178.28 (16)
O1—C1—C6—C5	−178.74 (14)	C7—C21—C22—C23	−60.4 (2)
C2—C1—C6—C5	−0.9 (3)	N2—C21—C22—C27	−121.55 (13)
O1—C1—C6—C7	−2.0 (2)	C28—C21—C22—C27	−1.08 (15)
C2—C1—C6—C7	175.85 (16)	C7—C21—C22—C27	120.27 (13)
C4—C5—C6—C1	1.5 (3)	C27—C22—C23—C24	−0.1 (2)
C4—C5—C6—C7	−175.15 (18)	C21—C22—C23—C24	−179.42 (15)
C1—C6—C7—C8	17.7 (2)	C22—C23—C24—C25	−0.3 (3)
C5—C6—C7—C8	−165.71 (14)	C23—C24—C25—C26	0.6 (3)
C1—C6—C7—C21	−102.30 (16)	C24—C25—C26—C27	−0.5 (2)
C5—C6—C7—C21	74.33 (18)	C25—C26—C27—C22	0.1 (2)
C6—C7—C8—N1	129.79 (13)	C25—C26—C27—N3	178.80 (15)
C21—C7—C8—N1	−105.62 (12)	C23—C22—C27—C26	0.2 (2)
C6—C7—C8—C16	−116.34 (13)	C21—C22—C27—C26	179.63 (14)
C21—C7—C8—C16	8.25 (13)	C23—C22—C27—N3	−178.70 (14)
C6—C7—C8—C9	6.41 (17)	C21—C22—C27—N3	0.74 (17)
C21—C7—C8—C9	131.00 (12)	N2—C21—C28—O4	−54.7 (2)
N1—C8—C9—O1	−167.40 (11)	C22—C21—C28—O4	−175.92 (15)
C16—C8—C9—O1	76.04 (14)	C7—C21—C28—O4	61.14 (19)
C7—C8—C9—O1	−43.05 (16)	N2—C21—C28—N3	122.35 (14)
N1—C8—C9—C10	−41.10 (17)	C22—C21—C28—N3	1.08 (16)
C16—C8—C9—C10	−157.65 (13)	C7—C21—C28—N3	−121.86 (14)
C7—C8—C9—C10	83.25 (16)	C16—C8—N1—O3	83.56 (15)
O1—C9—C10—C11	93.16 (18)	C7—C8—N1—O3	−163.55 (13)
C8—C9—C10—C11	−31.9 (2)	C9—C8—N1—O3	−36.28 (17)
O1—C9—C10—C15	−86.82 (16)	C16—C8—N1—O2	−91.57 (15)
C8—C9—C10—C15	148.08 (14)	C7—C8—N1—O2	21.31 (19)
C15—C10—C11—C12	−0.8 (3)	C9—C8—N1—O2	148.59 (14)
C9—C10—C11—C12	179.26 (16)	C17—C16—N2—C21	171.62 (12)
C10—C11—C12—C13	0.4 (3)	C8—C16—N2—C21	43.60 (13)
C11—C12—C13—C14	0.2 (3)	C17—C16—N2—C20	−59.32 (17)
C12—C13—C14—C15	−0.4 (3)	C8—C16—N2—C20	172.66 (12)
C13—C14—C15—C10	0.1 (3)	C22—C21—N2—C16	−162.76 (11)
C11—C10—C15—C14	0.5 (2)	C28—C21—N2—C16	83.23 (14)
C9—C10—C15—C14	−179.52 (16)	C7—C21—N2—C16	−38.06 (13)
N1—C8—C16—N2	86.17 (12)	C22—C21—N2—C20	69.69 (16)
C7—C8—C16—N2	−30.59 (13)	C28—C21—N2—C20	−44.32 (17)
C9—C8—C16—N2	−155.88 (11)	C7—C21—N2—C20	−165.61 (12)
N1—C8—C16—C17	−35.65 (17)	C19—C20—N2—C16	57.37 (19)
C7—C8—C16—C17	−152.41 (13)	C19—C20—N2—C21	−178.43 (14)
C9—C8—C16—C17	82.30 (16)	O4—C28—N3—C27	176.25 (15)
N2—C16—C17—C18	58.08 (17)	C21—C28—N3—C27	−0.72 (18)
C8—C16—C17—C18	176.04 (14)	C26—C27—N3—C28	−178.79 (16)
C16—C17—C18—C19	−57.7 (2)	C22—C27—N3—C28	0.01 (18)
C17—C18—C19—C20	56.6 (2)	C6—C1—O1—C9	−40.2 (2)
C18—C19—C20—N2	−55.2 (2)	C2—C1—O1—C9	141.90 (16)
C6—C7—C21—N2	141.84 (12)	C10—C9—O1—C1	−69.57 (16)
C8—C7—C21—N2	17.04 (13)	C8—C9—O1—C1	61.14 (16)
C6—C7—C21—C22	−94.34 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O4	0.98	2.50	3.1394 (18)	123
N3—H3A···O4ⁱ	0.86	1.97	2.8218 (17)	168

Symmetry code: (i) −x+3/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₅N₃O₄
M_r	467.51
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	23.2940 (13), 11.2517 (7), 19.7702 (10)
β (°)	112.659 (3)
V (Å³)	4781.8 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	20735, 5804, 3892
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.127, 1.00
No. of reflections	5804
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O4	0.98	2.50	3.1394 (18)	123
N3—H3A···O4ⁱ	0.86	1.97	2.8218 (17)	168

Symmetry code: (i) −x+3/2, −y+1/2, −z+1.

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SK,TS and DV acknowledge the UGC (SAP–CAS) for the departmental facilties. SK thanks DST PURSE for a Junior Research fellowship and TS thanks DST Inspire for a fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607. Web of Science PubMed Google Scholar
Colgan, S. T., Haggan, G. R. & Reed, R. H. (1996). J. Pharm. Biomed. Anal. 14, 825–833. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science 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
Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349–360. CAS PubMed Web of Science Google Scholar

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Volume 69| Part 6| June 2013| Page o993

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

6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octa­hydro­spiro­[chromeno[3,4-a]indol­izine-12,3′-indolin]-2′-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octahydrospiro[chromeno[3,4-a]indolizine-12,3′-indolin]-2′-one