1′,1′′-Dimethyl-4′-(4-methyl­phen­yl)di­spiro­[11H-indeno­[1,2-b]quinoxaline-11,2′-pyrrolidine-3′,3′′-piperidin]-4′′-one

Nagalakshmi, R.A.; Suresh, J.; Malathi, K.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536813022964

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1466

doi:10.1107/S1600536813022964

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1′,1′′-Dimethyl-4′-(4-methylphenyl)dispiro[11H-indeno[1,2-b]quinoxaline-11,2′-pyrrolidine-3′,3′′-piperidin]-4′′-one

R. A. Nagalakshmi,^a J. Suresh,^a K. Malathi,^b R. Ranjith Kumar ^b and P. L. N. Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 13 August 2013; accepted 15 August 2013; online 23 August 2013)

In the title compound, C₃₁H₃₀N₄O, the central pyrrolidine ring adopts an envelope conformation with the methylene C atom being the flap. The quinoxaline and indane rings are each planar, having r.m.s. deviations of 0.030 and 0.050 Å, respectively. The pyrrolidine ring mean plane forms dihedral angles of 88.25 (1) and 83.76 (1)° with the quinoxaline and indane rings, respectively. Intramolecular C—H⋯O and C—H⋯N interactions are observed. In the crystal, C—H⋯π interactions lead to helical supramolecular chains along the b-axis direction.

Related literature

For the importance of pyrrolidine compounds, see: Witherup et al. (1995 ). For the importance of heterocycles with piperidine sub-structures, see: El-Subbagh et al. (2000 ); Dimmock et al. (2001 ); Lee et al. (2001 ). For additional conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₃₁H₃₀N₄O
M_r = 474.59
Monoclinic, C 2/c
a = 22.3183 (7) Å
b = 14.4411 (5) Å
c = 17.2474 (6) Å
β = 116.547 (2)°
V = 4972.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.974
22517 measured reflections
4550 independent reflections
3034 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.124
S = 1.04
4550 reflections
327 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1	0.98	2.36	2.804 (2)	107
C41—H41B⋯N3	0.97	2.39	2.980 (2)	119
C11—H11⋯Cg1ⁱ	0.93	2.94	3.692 (2)	139
Symmetry code: (i) $[x, -y-1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813022964/tk5247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813022964/tk5247Isup2.hkl

checkCIF report

Comment top

Pyrrolidine-containing compounds are of significant importance because of their biological activities and widespread employment in catalysis (Witherup et al., 1995). Heterocycles with piperidine sub-structures display important biological activities, such as cytotoxic (El-Subbagh et al., 2000) and anti-cancer (Dimmock et al., 2001) besides being useful as synthons in the construction of alkaloid natural products (Lee et al., 2001). The high medicinal value of these compounds, in conjunction with our research interests, prompted us to synthesize and report the X-ray studies of the title compound.

In the title compound (Fig. 1), the central pyrrolidine ring is an envelope on C2 with asymmetry parameters ΔC_s(C2) = 7.1 (2)° and puckering parameters q₂ = 0.4303 (18) Å and ϕ₂ = 211.5 (2)° (Cremer & Pople, 1975). The quinoxaline and the indane group forms dihedral angles of 88.25 (1) and 83.76 (1)°, respectively, with the central pyrrolidine ring. The quinoxaline ring system (C12—C17/N3,N4) is planar, with r.m.s. deviation = 0.030 Å. The indane group is also planar with r.m.s deviation = 0.050 Å. The dihedral angle between the mean planes of the fused quinoxaline and the indane groups is 8.43 (1)°, indicate that the fused rings is slightly folded about the C12—C13 bond. The six-membered ring, N2/C41—C45, exhibits a twisted chair conformation, as indicated by the asymmetry parameters ΔC_s(N2) = 7.58 (16)°, ΔC_s(C45) = 7.58 (16)° and with the puckering parameters Q = 0.558 (2) Å, Θ = 164.1 (2)° and Φ = 207.1 (8)°. The torsion angle C4—C42—N2—C42 is -167.62 (16)° and corresponds to an antiperiplanar conformation. The sum of bond angles around N1(339.9°) and N2 (331.4°) indicate the atoms N1 and N2 are each in a pyramidal geometry. Weak intramolecular C—H···O, N interactions are observed (Table 1). In the crystal structure, C—H···π interactions, involving the benzene ring C14···C19, lead to the helical supramolecular chains along the b axis, as shown in Fig. 2.

Related literature top

For the importance of pyrrolidine compounds, see: Witherup et al. (1995). For the importance of heterocycles with piperidine sub-structures, see: El-Subbagh et al. (2000); Dimmock et al. (2001); Lee et al. (2001). For additional conformation analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of 1-methyl-3-[E-(4-methylphenyl)methylidene]tetrahydro-2(1H)- pyridinone (1 mmol), ninhydrin (1 mmol), o-phenylenediamine (1 mmol) and sarcosine (1 mmol) in methanol was refluxed for 3–4 h. After completion of the reaction as indicated by TLC the reaction mixture was poured into cold water. The solid precipitate obtained was filtered and dried. The product was purified by column chromatography using petroleum ether:ethylacetate mixture (90:10 v/v). Suitable crystals were obtained by recrystallizing the product from methanol. Yield: 37%, M. pt: 498–500 K.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. H-atoms are omitted for clarity.
	Fig. 2. The partial packing diagram showing C—H···π interactions as dashed lines. All H-atoms are omitted for clarity except for the H atom involved in the intermolecular interaction.

1',1''-Dimethyl-4'-(4-methylphenyl)dispiro[11H-indeno[1,2-b]quinoxaline-11,2'-pyrrolidine-3',3''-piperidin]-4''-one top

Crystal data top

C₃₁H₃₀N₄O	F(000) = 2016
M_r = 474.59	D_x = 1.268 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2000 reflections
a = 22.3183 (7) Å	θ = 2–31°
b = 14.4411 (5) Å	µ = 0.08 mm⁻¹
c = 17.2474 (6) Å	T = 293 K
β = 116.547 (2)°	Block, green
V = 4972.8 (3) Å³	0.21 × 0.19 × 0.18 mm
Z = 8

Data collection top

Bruker Kappa APEXII diffractometer	4550 independent reflections
Radiation source: fine-focus sealed tube	3034 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 0 pixels mm^-1	θ_max = 25.4°, θ_min = 2.0°
ω & \j scans	h = −26→25
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
T_min = 0.967, T_max = 0.974	l = −20→20
22517 measured reflections

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0634P)² + 0.8964P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4550 reflections	Δρ_max = 0.18 e Å⁻³
327 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (3)

Crystal data top

C₃₁H₃₀N₄O	V = 4972.8 (3) Å³
M_r = 474.59	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.3183 (7) Å	µ = 0.08 mm⁻¹
b = 14.4411 (5) Å	T = 293 K
c = 17.2474 (6) Å	0.21 × 0.19 × 0.18 mm
β = 116.547 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4550 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3034 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.031
22517 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.04	Δρ_max = 0.18 e Å⁻³
4550 reflections	Δρ_min = −0.12 e Å⁻³
327 parameters

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 F.² 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	0.19283 (9)	0.44011 (12)	0.17083 (12)	0.0662 (5)
H1A	0.1556	0.4180	0.1193	0.099*
H1B	0.2142	0.4902	0.1562	0.099*
H1C	0.1772	0.4614	0.2113	0.099*
C2	0.26183 (9)	0.31684 (11)	0.15307 (11)	0.0566 (4)
H2A	0.2837	0.3582	0.1293	0.068*
H2B	0.2245	0.2865	0.1060	0.068*
C3	0.31046 (8)	0.24719 (10)	0.21449 (10)	0.0515 (4)
H3	0.2835	0.2026	0.2282	0.062*
C4	0.35031 (8)	0.30452 (10)	0.29852 (10)	0.0497 (4)
C5	0.30037 (8)	0.38860 (10)	0.28912 (10)	0.0494 (4)
C6	0.28097 (8)	0.40162 (11)	0.36293 (11)	0.0522 (4)
C7	0.30097 (8)	0.48735 (12)	0.40302 (10)	0.0548 (4)
C8	0.28659 (10)	0.51283 (14)	0.47011 (11)	0.0694 (5)
H8	0.3003	0.5699	0.4972	0.083*
C9	0.25172 (11)	0.45217 (16)	0.49585 (13)	0.0780 (6)
H9	0.2422	0.4680	0.5414	0.094*
C10	0.23070 (10)	0.36849 (15)	0.45534 (12)	0.0714 (5)
H10	0.2065	0.3288	0.4733	0.086*
C11	0.24484 (9)	0.34188 (13)	0.38817 (11)	0.0615 (5)
H11	0.2303	0.2851	0.3607	0.074*
C12	0.32976 (8)	0.48350 (10)	0.28851 (10)	0.0489 (4)
C13	0.33176 (8)	0.53940 (11)	0.35792 (10)	0.0510 (4)
C14	0.37575 (8)	0.65677 (11)	0.31451 (11)	0.0554 (4)
C15	0.37010 (8)	0.60413 (11)	0.24282 (11)	0.0540 (4)
C16	0.39018 (9)	0.64307 (13)	0.18372 (12)	0.0653 (5)
H16	0.3863	0.6091	0.1359	0.078*
C17	0.41534 (10)	0.73044 (14)	0.19630 (15)	0.0768 (6)
H17	0.4282	0.7561	0.1566	0.092*
C18	0.42209 (10)	0.78177 (14)	0.26775 (15)	0.0787 (6)
H18	0.4400	0.8412	0.2759	0.094*
C19	0.40282 (10)	0.74624 (12)	0.32589 (13)	0.0688 (5)
H19	0.4076	0.7814	0.3735	0.083*
C31	0.35014 (8)	0.19158 (10)	0.17934 (11)	0.0518 (4)
C32	0.35959 (11)	0.21834 (12)	0.10931 (12)	0.0686 (5)
H32	0.3428	0.2751	0.0832	0.082*
C33	0.39341 (11)	0.16312 (14)	0.07647 (13)	0.0769 (6)
H33	0.3988	0.1840	0.0290	0.092*
C34	0.41901 (11)	0.07944 (15)	0.11128 (14)	0.0785 (6)
C35	0.40965 (15)	0.05333 (16)	0.18085 (18)	0.1093 (9)
H35	0.4264	−0.0036	0.2066	0.131*
C36	0.37650 (13)	0.10758 (14)	0.21450 (16)	0.0908 (7)
H36	0.3718	0.0866	0.2625	0.109*
C37	0.45532 (15)	0.0190 (2)	0.07414 (18)	0.1260 (10)
H37A	0.4938	−0.0084	0.1206	0.189*
H37B	0.4694	0.0560	0.0390	0.189*
H37C	0.4258	−0.0290	0.0393	0.189*
C41	0.41760 (8)	0.33778 (12)	0.30566 (11)	0.0563 (4)
H41A	0.4444	0.2846	0.3062	0.068*
H41B	0.4100	0.3751	0.2554	0.068*
C42	0.51060 (10)	0.44002 (16)	0.38092 (16)	0.0959 (7)
H42A	0.4946	0.4798	0.3311	0.144*
H42B	0.5410	0.3953	0.3771	0.144*
H42C	0.5334	0.4763	0.4325	0.144*
C43	0.47597 (11)	0.33179 (16)	0.45900 (13)	0.0862 (7)
H43A	0.5019	0.3672	0.5112	0.103*
H43B	0.5045	0.2835	0.4547	0.103*
C44	0.41635 (11)	0.28845 (15)	0.46469 (12)	0.0812 (6)
H44A	0.4321	0.2401	0.5083	0.097*
H44B	0.3944	0.3352	0.4834	0.097*
C45	0.36603 (10)	0.24775 (13)	0.38038 (12)	0.0633 (5)
N1	0.24057 (7)	0.36540 (9)	0.20961 (9)	0.0539 (4)
N2	0.45411 (7)	0.39221 (11)	0.38393 (10)	0.0678 (4)
N3	0.34651 (7)	0.51439 (9)	0.22985 (9)	0.0539 (4)
N4	0.35471 (7)	0.62400 (9)	0.37323 (9)	0.0581 (4)
O1	0.34059 (9)	0.17381 (10)	0.37835 (10)	0.0914 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0577 (11)	0.0755 (12)	0.0587 (12)	0.0110 (9)	0.0200 (10)	0.0029 (9)
C2	0.0560 (10)	0.0630 (10)	0.0429 (10)	−0.0017 (8)	0.0151 (9)	−0.0044 (8)
C3	0.0545 (10)	0.0525 (9)	0.0458 (10)	−0.0054 (8)	0.0207 (8)	0.0003 (7)
C4	0.0529 (10)	0.0545 (9)	0.0402 (9)	0.0012 (8)	0.0194 (8)	0.0015 (7)
C5	0.0488 (9)	0.0563 (9)	0.0410 (9)	−0.0019 (7)	0.0183 (8)	−0.0003 (7)
C6	0.0484 (10)	0.0637 (10)	0.0434 (10)	0.0044 (8)	0.0194 (8)	0.0042 (8)
C7	0.0516 (10)	0.0692 (11)	0.0409 (10)	0.0051 (8)	0.0182 (8)	0.0006 (8)
C8	0.0735 (13)	0.0864 (13)	0.0489 (11)	0.0002 (11)	0.0278 (11)	−0.0106 (9)
C9	0.0778 (14)	0.1113 (16)	0.0546 (12)	0.0052 (13)	0.0382 (12)	−0.0022 (11)
C10	0.0655 (13)	0.0987 (15)	0.0574 (12)	0.0015 (11)	0.0340 (11)	0.0109 (11)
C11	0.0584 (11)	0.0710 (11)	0.0551 (11)	−0.0014 (9)	0.0253 (10)	0.0046 (9)
C12	0.0459 (9)	0.0567 (9)	0.0388 (9)	0.0025 (7)	0.0142 (8)	0.0017 (7)
C13	0.0478 (9)	0.0570 (9)	0.0401 (9)	0.0044 (8)	0.0125 (8)	−0.0005 (7)
C14	0.0460 (10)	0.0554 (10)	0.0531 (11)	0.0040 (8)	0.0116 (9)	0.0055 (8)
C15	0.0452 (9)	0.0595 (10)	0.0488 (10)	0.0002 (8)	0.0135 (8)	0.0054 (8)
C16	0.0568 (11)	0.0755 (12)	0.0581 (11)	−0.0078 (10)	0.0206 (9)	0.0066 (9)
C17	0.0658 (13)	0.0817 (14)	0.0754 (15)	−0.0125 (11)	0.0249 (12)	0.0156 (11)
C18	0.0703 (13)	0.0621 (11)	0.0868 (16)	−0.0120 (10)	0.0200 (12)	0.0099 (11)
C19	0.0633 (12)	0.0571 (10)	0.0694 (13)	−0.0012 (9)	0.0148 (11)	−0.0001 (9)
C31	0.0562 (10)	0.0485 (9)	0.0479 (10)	−0.0066 (8)	0.0208 (9)	−0.0032 (7)
C32	0.0949 (15)	0.0591 (10)	0.0577 (12)	0.0070 (10)	0.0393 (12)	0.0031 (9)
C33	0.0916 (16)	0.0868 (14)	0.0614 (13)	0.0064 (12)	0.0424 (12)	−0.0036 (10)
C34	0.0772 (14)	0.0866 (14)	0.0653 (14)	0.0195 (12)	0.0261 (12)	−0.0074 (11)
C35	0.154 (3)	0.0787 (15)	0.117 (2)	0.0533 (16)	0.080 (2)	0.0320 (14)
C36	0.131 (2)	0.0701 (12)	0.0980 (18)	0.0313 (13)	0.0746 (17)	0.0290 (11)
C37	0.132 (2)	0.145 (2)	0.102 (2)	0.062 (2)	0.0533 (19)	−0.0064 (17)
C41	0.0504 (10)	0.0623 (10)	0.0505 (10)	0.0030 (8)	0.0175 (9)	−0.0039 (8)
C42	0.0582 (13)	0.1049 (17)	0.1071 (19)	−0.0202 (12)	0.0213 (13)	−0.0308 (14)
C43	0.0697 (14)	0.1080 (17)	0.0532 (13)	0.0155 (13)	0.0028 (11)	−0.0076 (11)
C44	0.0850 (15)	0.1026 (15)	0.0442 (12)	0.0253 (13)	0.0184 (11)	0.0128 (10)
C45	0.0728 (13)	0.0675 (11)	0.0522 (11)	0.0126 (10)	0.0302 (10)	0.0098 (9)
N1	0.0486 (8)	0.0615 (8)	0.0444 (8)	0.0015 (7)	0.0145 (7)	−0.0019 (6)
N2	0.0520 (9)	0.0787 (10)	0.0581 (10)	−0.0012 (8)	0.0116 (8)	−0.0140 (8)
N3	0.0557 (9)	0.0589 (8)	0.0449 (8)	−0.0018 (7)	0.0205 (7)	0.0019 (6)
N4	0.0559 (9)	0.0584 (8)	0.0507 (9)	0.0016 (7)	0.0154 (7)	−0.0038 (7)
O1	0.1314 (14)	0.0729 (9)	0.0757 (10)	−0.0015 (9)	0.0515 (10)	0.0191 (7)

Geometric parameters (Å, º) top

C1—N1	1.452 (2)	C16—C17	1.359 (3)
C1—H1A	0.9600	C16—H16	0.9300
C1—H1B	0.9600	C17—C18	1.387 (3)
C1—H1C	0.9600	C17—H17	0.9300
C2—N1	1.443 (2)	C18—C19	1.356 (3)
C2—C3	1.511 (2)	C18—H18	0.9300
C2—H2A	0.9700	C19—H19	0.9300
C2—H2B	0.9700	C31—C36	1.366 (2)
C3—C31	1.509 (2)	C31—C32	1.371 (2)
C3—C4	1.557 (2)	C32—C33	1.382 (3)
C3—H3	0.9800	C32—H32	0.9300
C4—C41	1.528 (2)	C33—C34	1.357 (3)
C4—C45	1.532 (2)	C33—H33	0.9300
C4—C5	1.607 (2)	C34—C35	1.360 (3)
C5—N1	1.462 (2)	C34—C37	1.515 (3)
C5—C12	1.521 (2)	C35—C36	1.372 (3)
C5—C6	1.528 (2)	C35—H35	0.9300
C6—C11	1.378 (2)	C36—H36	0.9300
C6—C7	1.391 (2)	C37—H37A	0.9600
C7—C8	1.382 (2)	C37—H37B	0.9600
C7—C13	1.456 (2)	C37—H37C	0.9600
C8—C9	1.371 (3)	C41—N2	1.456 (2)
C8—H8	0.9300	C41—H41A	0.9700
C9—C10	1.369 (3)	C41—H41B	0.9700
C9—H9	0.9300	C42—N2	1.459 (2)
C10—C11	1.384 (2)	C42—H42A	0.9600
C10—H10	0.9300	C42—H42B	0.9600
C11—H11	0.9300	C42—H42C	0.9600
C12—N3	1.3041 (19)	C43—N2	1.453 (3)
C12—C13	1.428 (2)	C43—C44	1.513 (3)
C13—N4	1.305 (2)	C43—H43A	0.9700
C14—N4	1.377 (2)	C43—H43B	0.9700
C14—C19	1.403 (2)	C44—C45	1.504 (3)
C14—C15	1.408 (2)	C44—H44A	0.9700
C15—N3	1.379 (2)	C44—H44B	0.9700
C15—C16	1.401 (2)	C45—O1	1.202 (2)

N1—C1—H1A	109.5	C19—C18—C17	120.68 (18)
N1—C1—H1B	109.5	C19—C18—H18	119.7
H1A—C1—H1B	109.5	C17—C18—H18	119.7
N1—C1—H1C	109.5	C18—C19—C14	120.28 (19)
H1A—C1—H1C	109.5	C18—C19—H19	119.9
H1B—C1—H1C	109.5	C14—C19—H19	119.9
N1—C2—C3	101.52 (13)	C36—C31—C32	115.86 (16)
N1—C2—H2A	111.5	C36—C31—C3	120.51 (15)
C3—C2—H2A	111.5	C32—C31—C3	123.56 (15)
N1—C2—H2B	111.5	C31—C32—C33	121.72 (17)
C3—C2—H2B	111.5	C31—C32—H32	119.1
H2A—C2—H2B	109.3	C33—C32—H32	119.1
C31—C3—C2	116.05 (13)	C34—C33—C32	122.13 (18)
C31—C3—C4	117.60 (14)	C34—C33—H33	118.9
C2—C3—C4	103.36 (12)	C32—C33—H33	118.9
C31—C3—H3	106.3	C33—C34—C35	115.91 (18)
C2—C3—H3	106.3	C33—C34—C37	121.7 (2)
C4—C3—H3	106.3	C35—C34—C37	122.4 (2)
C41—C4—C45	106.37 (14)	C34—C35—C36	122.7 (2)
C41—C4—C3	111.96 (12)	C34—C35—H35	118.7
C45—C4—C3	111.94 (13)	C36—C35—H35	118.7
C41—C4—C5	112.52 (12)	C31—C36—C35	121.73 (19)
C45—C4—C5	111.13 (12)	C31—C36—H36	119.1
C3—C4—C5	103.06 (12)	C35—C36—H36	119.1
N1—C5—C12	114.56 (13)	C34—C37—H37A	109.5
N1—C5—C6	109.26 (13)	C34—C37—H37B	109.5
C12—C5—C6	100.27 (12)	H37A—C37—H37B	109.5
N1—C5—C4	102.87 (12)	C34—C37—H37C	109.5
C12—C5—C4	113.56 (12)	H37A—C37—H37C	109.5
C6—C5—C4	116.79 (12)	H37B—C37—H37C	109.5
C11—C6—C7	120.22 (15)	N2—C41—C4	111.52 (13)
C11—C6—C5	127.58 (15)	N2—C41—H41A	109.3
C7—C6—C5	112.10 (14)	C4—C41—H41A	109.3
C8—C7—C6	120.69 (16)	N2—C41—H41B	109.3
C8—C7—C13	130.67 (16)	C4—C41—H41B	109.3
C6—C7—C13	108.49 (13)	H41A—C41—H41B	108.0
C9—C8—C7	118.62 (18)	N2—C42—H42A	109.5
C9—C8—H8	120.7	N2—C42—H42B	109.5
C7—C8—H8	120.7	H42A—C42—H42B	109.5
C10—C9—C8	120.89 (17)	N2—C42—H42C	109.5
C10—C9—H9	119.6	H42A—C42—H42C	109.5
C8—C9—H9	119.6	H42B—C42—H42C	109.5
C9—C10—C11	121.17 (18)	N2—C43—C44	110.57 (17)
C9—C10—H10	119.4	N2—C43—H43A	109.5
C11—C10—H10	119.4	C44—C43—H43A	109.5
C6—C11—C10	118.38 (17)	N2—C43—H43B	109.5
C6—C11—H11	120.8	C44—C43—H43B	109.5
C10—C11—H11	120.8	H43A—C43—H43B	108.1
N3—C12—C13	123.00 (14)	C45—C44—C43	113.41 (16)
N3—C12—C5	125.97 (14)	C45—C44—H44A	108.9
C13—C12—C5	110.83 (13)	C43—C44—H44A	108.9
N4—C13—C12	124.14 (15)	C45—C44—H44B	108.9
N4—C13—C7	127.68 (15)	C43—C44—H44B	108.9
C12—C13—C7	108.10 (14)	H44A—C44—H44B	107.7
N4—C14—C19	118.75 (16)	O1—C45—C44	120.93 (18)
N4—C14—C15	122.30 (15)	O1—C45—C4	122.54 (18)
C19—C14—C15	118.95 (16)	C44—C45—C4	116.52 (17)
N3—C15—C16	118.83 (16)	C2—N1—C1	116.41 (13)
N3—C15—C14	121.84 (15)	C2—N1—C5	107.90 (12)
C16—C15—C14	119.32 (16)	C1—N1—C5	115.85 (13)
C17—C16—C15	120.02 (19)	C43—N2—C41	109.14 (15)
C17—C16—H16	120.0	C43—N2—C42	111.38 (17)
C15—C16—H16	120.0	C41—N2—C42	110.91 (15)
C16—C17—C18	120.73 (19)	C12—N3—C15	114.63 (14)
C16—C17—H17	119.6	C13—N4—C14	113.89 (14)
C18—C17—H17	119.6

N1—C2—C3—C31	−172.10 (13)	C14—C15—C16—C17	0.6 (3)
N1—C2—C3—C4	−41.85 (15)	C15—C16—C17—C18	0.6 (3)
C31—C3—C4—C41	30.84 (19)	C16—C17—C18—C19	−0.9 (3)
C2—C3—C4—C41	−98.47 (15)	C17—C18—C19—C14	0.0 (3)
C31—C3—C4—C45	−88.50 (17)	N4—C14—C19—C18	−177.93 (16)
C2—C3—C4—C45	142.19 (14)	C15—C14—C19—C18	1.1 (3)
C31—C3—C4—C5	152.00 (13)	C2—C3—C31—C36	−156.72 (18)
C2—C3—C4—C5	22.69 (14)	C4—C3—C31—C36	80.2 (2)
C41—C4—C5—N1	124.83 (13)	C2—C3—C31—C32	20.2 (2)
C45—C4—C5—N1	−116.00 (15)	C4—C3—C31—C32	−102.9 (2)
C3—C4—C5—N1	4.05 (14)	C36—C31—C32—C33	0.3 (3)
C41—C4—C5—C12	0.45 (18)	C3—C31—C32—C33	−176.66 (18)
C45—C4—C5—C12	119.62 (15)	C31—C32—C33—C34	0.2 (3)
C3—C4—C5—C12	−120.33 (13)	C32—C33—C34—C35	−0.3 (3)
C41—C4—C5—C6	−115.54 (15)	C32—C33—C34—C37	179.3 (2)
C45—C4—C5—C6	3.63 (19)	C33—C34—C35—C36	0.0 (4)
C3—C4—C5—C6	123.68 (14)	C37—C34—C35—C36	−179.6 (3)
N1—C5—C6—C11	51.5 (2)	C32—C31—C36—C35	−0.7 (3)
C12—C5—C6—C11	172.17 (17)	C3—C31—C36—C35	176.4 (2)
C4—C5—C6—C11	−64.7 (2)	C34—C35—C36—C31	0.6 (4)
N1—C5—C6—C7	−125.00 (15)	C45—C4—C41—N2	−58.10 (18)
C12—C5—C6—C7	−4.29 (17)	C3—C4—C41—N2	179.34 (13)
C4—C5—C6—C7	118.85 (16)	C5—C4—C41—N2	63.81 (17)
C11—C6—C7—C8	1.8 (3)	N2—C43—C44—C45	48.0 (2)
C5—C6—C7—C8	178.55 (15)	C43—C44—C45—O1	137.3 (2)
C11—C6—C7—C13	−174.11 (15)	C43—C44—C45—C4	−41.7 (2)
C5—C6—C7—C13	2.64 (19)	C41—C4—C45—O1	−134.21 (18)
C6—C7—C8—C9	−0.5 (3)	C3—C4—C45—O1	−11.6 (2)
C13—C7—C8—C9	174.35 (18)	C5—C4—C45—O1	103.01 (19)
C7—C8—C9—C10	−0.9 (3)	C41—C4—C45—C44	44.83 (19)
C8—C9—C10—C11	1.0 (3)	C3—C4—C45—C44	167.41 (15)
C7—C6—C11—C10	−1.6 (3)	C5—C4—C45—C44	−77.95 (19)
C5—C6—C11—C10	−177.83 (17)	C3—C2—N1—C1	179.32 (13)
C9—C10—C11—C6	0.2 (3)	C3—C2—N1—C5	47.10 (16)
N1—C5—C12—N3	−53.7 (2)	C12—C5—N1—C2	92.15 (15)
C6—C5—C12—N3	−170.56 (15)	C6—C5—N1—C2	−156.30 (13)
C4—C5—C12—N3	64.1 (2)	C4—C5—N1—C2	−31.57 (15)
N1—C5—C12—C13	121.29 (15)	C12—C5—N1—C1	−40.37 (18)
C6—C5—C12—C13	4.46 (17)	C6—C5—N1—C1	71.18 (16)
C4—C5—C12—C13	−120.91 (14)	C4—C5—N1—C1	−164.10 (13)
N3—C12—C13—N4	−5.0 (3)	C44—C43—N2—C41	−61.5 (2)
C5—C12—C13—N4	179.81 (15)	C44—C43—N2—C42	175.73 (17)
N3—C12—C13—C7	171.94 (15)	C4—C41—N2—C43	69.31 (18)
C5—C12—C13—C7	−3.26 (18)	C4—C41—N2—C42	−167.62 (16)
C8—C7—C13—N4	1.8 (3)	C13—C12—N3—C15	3.6 (2)
C6—C7—C13—N4	177.18 (16)	C5—C12—N3—C15	178.01 (14)
C8—C7—C13—C12	−174.98 (18)	C16—C15—N3—C12	179.20 (15)
C6—C7—C13—C12	0.39 (19)	C14—C15—N3—C12	0.5 (2)
N4—C14—C15—N3	−3.7 (3)	C12—C13—N4—C14	1.6 (2)
C19—C14—C15—N3	177.29 (15)	C7—C13—N4—C14	−174.70 (15)
N4—C14—C15—C16	177.59 (16)	C19—C14—N4—C13	−178.54 (15)
C19—C14—C15—C16	−1.4 (2)	C15—C14—N4—C13	2.4 (2)
N3—C15—C16—C17	−178.18 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.98	2.36	2.804 (2)	107
C41—H41B···N3	0.97	2.39	2.980 (2)	119
C11—H11···Cg1ⁱ	0.93	2.94	3.692 (2)	139

Symmetry code: (i) x, −y−1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.98	2.36	2.804 (2)	107
C41—H41B···N3	0.97	2.39	2.980 (2)	119
C11—H11···Cg1ⁱ	0.93	2.94	3.692 (2)	139

Symmetry code: (i) x, −y−1, z−1/2.

Acknowledgements

JS and RAN thank the management of the Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under their fast-track scheme (No. SR/FT/CS-073/2009)

References

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

1′,1′′-Di­methyl-4′-(4-methyl­phen­yl)di­spiro­[11H-indeno­[1,2-b]quinoxaline-11,2′-pyrrolidine-3′,3′′-piperidin]-4′′-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

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organic compounds

1′,1′′-Dimethyl-4′-(4-methylphenyl)dispiro[11H-indeno[1,2-b]quinoxaline-11,2′-pyrrolidine-3′,3′′-piperidin]-4′′-one