{1′-Phenyl-1′,2′,5′,6′,7′,7a'-hexa­hydro­spiro­[indeno­[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tol­yl)methanone

Srinivasan, T.; Suhitha, S.; Purushothaman, S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536812031480

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2469

https://doi.org/10.1107/S1600536812031480

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{1′-Phenyl-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tolyl)methanone

T. Srinivasan,^a S. Suhitha,^a S. Purushothaman,^b R. Raghunathan ^b and D. 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 25 June 2012; accepted 10 July 2012; online 18 July 2012)

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 envelope conformation. 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

C₃₅H₂₉N₃O
M_r = 507.61
Orthorhombic, P b c a
a = 16.4102 (6) Å
b = 16.4371 (6) Å
c = 20.0648 (7) Å
V = 5412.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
47718 measured reflections
6643 independent reflections
3751 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.144
S = 1.01
6643 reflections
363 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031480/bt5959sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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 top

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 column chromatography using petroleum ether/ethyl acetate (4:1) as eluent.

Structure description top

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).;

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The crystal packing of the title compound viewed down a axis. H-atoms not involved in H-bonds have been excluded for clarity.

{1'-Phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline- 11,3'-pyrrolizin]-2'-yl}(p-tolyl)methanone top

Crystal data top

C₃₅H₂₉N₃O	F(000) = 2144
M_r = 507.61	D_x = 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

Data collection top

Bruker SMART APEXII area-detector diffractometer	3751 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 28.3°, θ_min = 2.0°
ω and φ scans	h = −18→21
47718 measured reflections	k = −21→21
6643 independent reflections	l = −25→26

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0614P)² + 1.0312P] where P = (F_o² + 2F_c²)/3
6643 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.26 e Å⁻³
3 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₃₅H₂₉N₃O	V = 5412.2 (3) Å³
M_r = 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

Data collection top

Bruker SMART APEXII area-detector diffractometer	3751 reflections with I > 2σ(I)
47718 measured reflections	R_int = 0.044
6643 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.01	Δρ_max = 0.26 e Å⁻³
6643 reflections	Δρ_min = −0.25 e Å⁻³
363 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	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

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

{1′-Phenyl-1′,2′,5′,6′,7′,7a'-hexa­hydro­spiro­[indeno­[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tol­yl)methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

{1′-Phenyl-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tolyl)methanone