Crystal structure of 1′,1′′-dimethyl-4′-(4-cholorophen­yl)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/S2056989014027698

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o68-o69

doi:10.1107/S2056989014027698

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Crystal structure of 1′,1′′-dimethyl-4′-(4-cholorophenyl)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. Nilantha 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

Edited by O. Blacque, University of Zürich, Switzerland (Received 27 November 2014; accepted 19 December 2014; online 3 January 2015)

In the title compound, C₃₀H₂₇ClN₄O, the central pyrrolidine ring adopts an envelope conformation with the methylene C atom being the flap. The quinoxaline and indane rings are each essentially planar, with r.m.s. deviations of 0.027 (1) and 0.0417 (1) Å, respectively. The pyrrolidine ring forms dihedral angles of 88.25 (1) and 83.76 (1)° with the quinoxaline and indane rings, respectively. A weak intramolecular C—H⋯N interaction is observed. In the crystal, C—H⋯π interactions lead to supramolecular chains along [101] that assemble in the ac plane. Connections along the b axis are of the type Cl⋯Cl [3.6538 (16) Å].

Keywords: crystal structure; quinoxaline derivative; intramolecular C—H⋯N interaction; C—H⋯π interaction; Cl⋯Cl contact.

CCDC reference: 1040368

1. Related literature

For the importance of quinoxaline derivatives, see: Abasolo et al. (1987 ); Kleim et al. (1995 ); Dailey et al. (2001 ); Rodrigo et al. (2002 ); Seitz et al. (2002 ). For a related structure, see: Selvanayagam et al. (2011 ).

2. Experimental

2.1. Crystal data

C₃₀H₂₇ClN₄O
M_r = 495.00
Monoclinic, C 2/c
a = 22.4220 (13) Å
b = 14.3498 (9) Å
c = 17.2811 (9) Å
β = 116.847 (2)°
V = 4960.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.18 mm

2.2. Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.974
18093 measured reflections
3791 independent reflections
2758 reflections with I > 2σ(I)
R_int = 0.032

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.116
S = 1.05
3791 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C41—H41A⋯N3	0.97	2.39	2.988 (3)	120
C11—H11⋯Cg1ⁱ	0.93	2.89	3.655 (2)	140
Symmetry code: (i) $[x, -y, z-{\script{1\over 2}}]$ .

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: SHELXL2014 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1040368

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989014027698/zq2230sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989014027698/zq2230Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989014027698/zq2230Isup3.cml

checkCIF report

Chemical context top

Quinoxaline derivatives are an important class of benzoheterocycles. They have found applications as anti-cancer, anti-viral, and anti-bacterial agents (Seitz et al., 2002), and dyes (Dailey et al., 2001). Quinoxaline derivatives were found to exhibit anti-microbial (Kleim et al. 1995), antitumor (Abasolo et al., 1987), and anti-tuberculous activity (Rodrigo et al., 2002). Our interest in preparing pharmacologically active quinoxaline derivatives led us to the title compound, and we have undertaken X-ray crystal structure determination in order to establish its conformation.

Structural commentary top

In the title compound (Fig. 1), C₃₀H₂₇ClN₄O, the central pyrrolidine ring is an envelope on C2 with the asymmetry parameters ΔC_s(C2) = 7.6 (2) Å and puckering parameters q₂ = 0.433 (2) Å and ϕ₂ = 31.2 (3)°. The pyrrolidine ring is almost equatorial with the quinoxaline and indane rings making dihedral angles of 88.34 (1)° and 83.71 (1)°, respectively. The quinoxaline ring system (C12—C17/N3,N4) is planar, with r.m.s. deviation of 0.027 (1) Å. The indane group is also planar with r.m.s.deviation 0.0417 (1)°. The dihedral angle between the mean planes of the fused quinoxaline and the indane groups is 8.39 (1) °, which indicates that the fused rings are slightly twisted about the C12—C13 bond. The C—C bond lengths in the pyrrolidine ring in particular, at two spiro junctions (C3—C4 = 1.558 (3) Å and C4—C5 = 1.605 (3) Å) are somewhat longer than the normal values (C—C = 1.54 Å), as found in a similar structure (Selvanayagam et al., 2011). This may be due to the the steric interactions of the bulky substituents at atoms C4 and C5 of the pyrrolidine ring. The short contact H32 ··· H2b of 2.18 Å results in substantial widening of the bond angle C3—C31—C32 to 123.67 (1) °. The sum of the bond angles around N1 (339.87 (1)°) and N2 (330.97 (1)°) indicate that the atoms N1 and N2 exhibit a pyramidal geometry. The six membered ring N2/C41—C45 exhibits a twisted chair conformation, as indicated by the assymetrical parameters ΔC_s(N2) = 7.4 (2)°, ΔC_s(C45) = 7.4 (2) ° and with the puckering parameters Q = 0.559 (3) Å, θ = 17.4 (3)° and Φ = 24.6 (9)°. The torsion angle C4—C41—N2—C42 is -167.50 ° corresponds to an antiperiplanar conformation.

A weak intra-molecular C—H···N interaction is observed (Table 1). In the crystal, C—H···π interactions lead to supramolecular chains along [101] that assemble in the ac plane. Connections along the b axis are of the type Cl···Cl (3.6538 (16) Å).

Synthesis and crystallization top

A mixture of 1-methyl-3-[E-(4-chlorophenyl)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 colum chromatography using petroleum ether:ethylacetate mixture (90:10 V/V). Suitable crystals for the single crystal-X-ray studies were obtained by recrystalizing the product from methanol. Yield: 42%, Melting point: 450-452 K.

Refinement top

All the H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.98 Å, and with U_iso = 1.2U_eq(C) for CH₂ and CH groups, and U_iso = 1.5U_eq(C) for CH₃ groups. The (-1 1 1), (1 1 0) reflections were affected by the beam-stop and were removed from the final refinement. The best crystal investigated was still of poor quality and very weakly diffracting, with no usable data obtanied above θ = 23.8°. Nonetheless, the structure was solved readily and refined to give acceptable uncertainties on the metrical data.

Related literature top

For the importance of quinoxaline derivatives, see: Abasolo et al. (1987); Kleim et al. (1995); Dailey et al. (2001); Rodrigo et al. (2002); Seitz et al. (2002). For a related structure, see: Selvanayagam et al. (2011).

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: SHELXL2014 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, 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-cholorophenyl)dispiro[11H- indeno[1,2-b]quinoxaline-11,2'-pyrrolidine-3',3''-piperidin]-4''-one top

Crystal data top

C₃₀H₂₇ClN₄O	F(000) = 2080
M_r = 495.00	D_x = 1.326 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.4220 (13) Å	Cell parameters from 2000 reflections
b = 14.3498 (9) Å	θ = 2–31°
c = 17.2811 (9) Å	µ = 0.19 mm⁻¹
β = 116.847 (2)°	T = 293 K
V = 4960.9 (5) Å³	Block, colourless
Z = 8	0.21 × 0.19 × 0.18 mm

Data collection top

Bruker Kappa APEXII diffractometer	2758 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
ω and ϕ scans	θ_max = 23.8°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→25
T_min = 0.967, T_max = 0.974	k = −16→16
18093 measured reflections	l = −19→13
3791 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.052P)² + 2.7359P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3791 reflections	Δρ_max = 0.22 e Å⁻³
325 parameters	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₃₀H₂₇ClN₄O	V = 4960.9 (5) Å³
M_r = 495.00	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.4220 (13) Å	µ = 0.19 mm⁻¹
b = 14.3498 (9) Å	T = 293 K
c = 17.2811 (9) Å	0.21 × 0.19 × 0.18 mm
β = 116.847 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	3791 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2758 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.032
18093 measured reflections	θ_max = 23.8°

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
3791 reflections	Δρ_min = −0.26 e Å⁻³
325 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.

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

	x	y	z	U_iso*/U_eq
C1	0.30822 (11)	0.05687 (16)	0.33108 (14)	0.0608 (6)
H1A	0.3191	0.0297	0.2883	0.091*
H1B	0.3481	0.0807	0.3781	0.091*
H1C	0.2888	0.0103	0.3526	0.091*
C2	0.23954 (11)	0.18035 (15)	0.34879 (13)	0.0523 (5)
H2A	0.2767	0.2104	0.3965	0.063*
H2B	0.2174	0.1385	0.3717	0.063*
C3	0.19136 (10)	0.25089 (14)	0.28740 (12)	0.0459 (5)
H3	0.2184	0.2962	0.2746	0.055*
C4	0.15164 (10)	0.19405 (14)	0.20256 (12)	0.0457 (5)
C5	0.20122 (9)	0.10932 (14)	0.21204 (12)	0.0439 (5)
C6	0.22053 (10)	0.09623 (14)	0.13862 (12)	0.0466 (5)
C7	0.19965 (10)	0.01074 (15)	0.09751 (12)	0.0492 (5)
C8	0.21358 (12)	−0.01455 (18)	0.03003 (14)	0.0630 (6)
H8	0.1994	−0.0717	0.0024	0.076*
C9	0.24862 (13)	0.0464 (2)	0.00475 (16)	0.0714 (7)
H9	0.2575	0.0308	−0.0413	0.086*
C10	0.27083 (12)	0.13009 (18)	0.04655 (14)	0.0650 (6)
H10	0.2953	0.1699	0.0292	0.078*
C11	0.25718 (10)	0.15583 (16)	0.11420 (13)	0.0556 (6)
H11	0.2725	0.2124	0.1426	0.067*
C12	0.17122 (9)	0.01365 (14)	0.21185 (12)	0.0447 (5)
C13	0.16878 (10)	−0.04160 (14)	0.14202 (12)	0.0462 (5)
C14	0.12375 (10)	−0.15970 (15)	0.18401 (13)	0.0513 (5)
C15	0.12990 (10)	−0.10743 (15)	0.25619 (13)	0.0506 (5)
C16	0.11002 (11)	−0.14672 (17)	0.31511 (15)	0.0628 (6)
H16	0.1147	−0.1130	0.3635	0.075*
C17	0.08385 (12)	−0.23439 (19)	0.30153 (17)	0.0719 (7)
H17	0.0710	−0.2604	0.3410	0.086*
C18	0.07626 (12)	−0.28531 (18)	0.22925 (18)	0.0737 (7)
H18	0.0576	−0.3446	0.2202	0.088*
C19	0.09589 (11)	−0.24923 (16)	0.17162 (15)	0.0623 (6)
H19	0.0908	−0.2842	0.1237	0.075*
C31	0.15093 (10)	0.30600 (14)	0.32168 (13)	0.0483 (5)
C32	0.14179 (12)	0.27914 (17)	0.39179 (14)	0.0640 (6)
H32	0.1598	0.2228	0.4188	0.077*
C33	0.10678 (13)	0.3330 (2)	0.42345 (15)	0.0742 (7)
H33	0.1012	0.3126	0.4709	0.089*
C34	0.08049 (13)	0.4154 (2)	0.38554 (17)	0.0752 (7)
C35	0.08847 (17)	0.4439 (2)	0.3162 (2)	0.1013 (10)
H35	0.0704	0.5005	0.2898	0.122*
C36	0.12311 (15)	0.38969 (18)	0.28474 (18)	0.0839 (8)
H36	0.1278	0.4104	0.2368	0.101*
C41	0.08396 (10)	0.16135 (16)	0.19371 (13)	0.0539 (5)
H41A	0.0908	0.1229	0.2432	0.065*
H41B	0.0576	0.2151	0.1934	0.065*
C42	−0.00945 (13)	0.0602 (2)	0.1155 (2)	0.0974 (10)
H42A	0.0060	0.0193	0.1647	0.146*
H42B	−0.0396	0.1053	0.1193	0.146*
H42C	−0.0322	0.0244	0.0632	0.146*
C43	0.02670 (14)	0.1710 (2)	0.04037 (16)	0.0857 (9)
H43A	−0.0012	0.2199	0.0455	0.103*
H43B	0.0004	0.1369	−0.0128	0.103*
C44	0.08668 (14)	0.2140 (2)	0.03617 (14)	0.0824 (8)
H44A	0.1079	0.1672	0.0164	0.099*
H44B	0.0716	0.2639	−0.0063	0.099*
C45	0.13753 (13)	0.25230 (18)	0.12140 (14)	0.0612 (6)
N1	0.26100 (8)	0.13210 (12)	0.29228 (10)	0.0486 (4)
N2	0.04763 (9)	0.10806 (14)	0.11417 (12)	0.0668 (5)
N3	0.15437 (8)	−0.01733 (12)	0.27018 (10)	0.0499 (4)
N4	0.14498 (8)	−0.12662 (12)	0.12568 (11)	0.0532 (5)
O1	0.16569 (11)	0.32522 (13)	0.12566 (11)	0.0874 (6)
Cl1	0.03708 (5)	0.48362 (8)	0.42608 (6)	0.1348 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0526 (13)	0.0683 (16)	0.0540 (13)	0.0102 (11)	0.0175 (11)	0.0012 (11)
C2	0.0550 (13)	0.0562 (13)	0.0397 (11)	0.0015 (10)	0.0160 (10)	−0.0042 (10)
C3	0.0513 (12)	0.0446 (12)	0.0423 (11)	−0.0033 (9)	0.0215 (10)	−0.0010 (9)
C4	0.0502 (12)	0.0497 (13)	0.0360 (10)	0.0035 (10)	0.0185 (9)	0.0018 (9)
C5	0.0458 (11)	0.0479 (12)	0.0362 (10)	0.0004 (9)	0.0168 (9)	−0.0014 (9)
C6	0.0451 (11)	0.0539 (13)	0.0382 (11)	0.0029 (10)	0.0164 (9)	0.0037 (10)
C7	0.0484 (12)	0.0581 (14)	0.0380 (11)	0.0033 (10)	0.0167 (10)	−0.0017 (10)
C8	0.0732 (16)	0.0713 (16)	0.0464 (13)	−0.0009 (13)	0.0287 (12)	−0.0120 (11)
C9	0.0785 (17)	0.094 (2)	0.0515 (14)	0.0000 (15)	0.0383 (13)	−0.0059 (14)
C10	0.0638 (15)	0.0843 (19)	0.0534 (14)	−0.0014 (13)	0.0322 (12)	0.0078 (13)
C11	0.0566 (13)	0.0617 (15)	0.0488 (12)	−0.0004 (11)	0.0241 (11)	0.0025 (11)
C12	0.0424 (11)	0.0516 (13)	0.0371 (11)	0.0039 (9)	0.0153 (9)	0.0017 (9)
C13	0.0440 (11)	0.0480 (13)	0.0402 (11)	0.0032 (10)	0.0133 (9)	0.0003 (10)
C14	0.0428 (11)	0.0502 (14)	0.0500 (12)	0.0033 (10)	0.0112 (10)	0.0067 (10)
C15	0.0408 (11)	0.0565 (14)	0.0470 (12)	−0.0002 (10)	0.0133 (10)	0.0055 (10)
C16	0.0532 (13)	0.0751 (17)	0.0574 (14)	−0.0066 (12)	0.0226 (11)	0.0095 (12)
C17	0.0577 (15)	0.0799 (19)	0.0707 (17)	−0.0117 (13)	0.0223 (13)	0.0178 (14)
C18	0.0583 (15)	0.0604 (16)	0.0869 (19)	−0.0086 (12)	0.0190 (14)	0.0120 (15)
C19	0.0554 (14)	0.0506 (14)	0.0665 (15)	−0.0019 (11)	0.0149 (12)	0.0030 (11)
C31	0.0535 (12)	0.0455 (13)	0.0454 (12)	−0.0062 (10)	0.0218 (10)	−0.0037 (9)
C32	0.0822 (17)	0.0618 (15)	0.0521 (13)	0.0109 (13)	0.0339 (13)	0.0044 (11)
C33	0.0803 (17)	0.098 (2)	0.0518 (14)	0.0089 (16)	0.0364 (14)	−0.0049 (14)
C34	0.0730 (17)	0.085 (2)	0.0645 (16)	0.0170 (15)	0.0286 (14)	−0.0128 (14)
C35	0.143 (3)	0.0686 (19)	0.120 (3)	0.0444 (19)	0.084 (2)	0.0252 (18)
C36	0.122 (2)	0.0625 (17)	0.096 (2)	0.0280 (16)	0.0741 (19)	0.0268 (15)
C41	0.0477 (12)	0.0577 (14)	0.0505 (12)	0.0040 (10)	0.0170 (10)	−0.0077 (10)
C42	0.0565 (16)	0.100 (2)	0.111 (2)	−0.0149 (15)	0.0164 (16)	−0.0301 (18)
C43	0.0708 (18)	0.103 (2)	0.0537 (15)	0.0192 (16)	0.0022 (14)	−0.0080 (15)
C44	0.090 (2)	0.103 (2)	0.0409 (13)	0.0323 (17)	0.0177 (14)	0.0129 (13)
C45	0.0720 (16)	0.0648 (16)	0.0493 (13)	0.0192 (13)	0.0295 (12)	0.0092 (12)
N1	0.0462 (10)	0.0531 (11)	0.0410 (9)	0.0039 (8)	0.0148 (8)	−0.0023 (8)
N2	0.0516 (11)	0.0734 (14)	0.0582 (12)	0.0014 (10)	0.0096 (10)	−0.0157 (10)
N3	0.0496 (10)	0.0564 (12)	0.0424 (10)	−0.0024 (8)	0.0198 (8)	0.0016 (8)
N4	0.0516 (10)	0.0521 (11)	0.0475 (10)	0.0005 (9)	0.0151 (9)	−0.0010 (9)
O1	0.1327 (17)	0.0656 (12)	0.0729 (12)	0.0032 (12)	0.0542 (12)	0.0171 (10)
Cl1	0.1370 (8)	0.1672 (9)	0.1083 (7)	0.0676 (7)	0.0626 (6)	−0.0185 (6)

Geometric parameters (Å, º) top

C1—N1	1.447 (3)	C15—C16	1.401 (3)
C1—H1A	0.9600	C16—C17	1.363 (3)
C1—H1B	0.9600	C16—H16	0.9300
C1—H1C	0.9600	C17—C18	1.390 (4)
C2—N1	1.445 (2)	C17—H17	0.9300
C2—C3	1.511 (3)	C18—C19	1.360 (3)
C2—H2A	0.9700	C18—H18	0.9300
C2—H2B	0.9700	C19—H19	0.9300
C3—C31	1.511 (3)	C31—C36	1.371 (3)
C3—C4	1.558 (3)	C31—C32	1.372 (3)
C3—H3	0.9800	C32—C33	1.379 (3)
C4—C41	1.529 (3)	C32—H32	0.9300
C4—C45	1.538 (3)	C33—C34	1.352 (4)
C4—C5	1.605 (3)	C33—H33	0.9300
C5—N1	1.466 (2)	C34—C35	1.352 (4)
C5—C6	1.526 (3)	C34—Cl1	1.736 (2)
C5—C12	1.528 (3)	C35—C36	1.374 (4)
C6—C11	1.378 (3)	C35—H35	0.9300
C6—C7	1.389 (3)	C36—H36	0.9300
C7—C8	1.385 (3)	C41—N2	1.458 (3)
C7—C13	1.455 (3)	C41—H41A	0.9700
C8—C9	1.372 (3)	C41—H41B	0.9700
C8—H8	0.9300	C42—N2	1.462 (3)
C9—C10	1.374 (3)	C42—H42A	0.9600
C9—H9	0.9300	C42—H42B	0.9600
C10—C11	1.386 (3)	C42—H42C	0.9600
C10—H10	0.9300	C43—N2	1.457 (3)
C11—H11	0.9300	C43—C44	1.511 (4)
C12—N3	1.304 (2)	C43—H43A	0.9700
C12—C13	1.424 (3)	C43—H43B	0.9700
C13—N4	1.310 (3)	C44—C45	1.501 (4)
C14—N4	1.379 (3)	C44—H44A	0.9700
C14—C19	1.402 (3)	C44—H44B	0.9700
C14—C15	1.408 (3)	C45—O1	1.207 (3)
C15—N3	1.382 (3)

N1—C1—H1A	109.5	C16—C17—C18	120.6 (2)
N1—C1—H1B	109.5	C16—C17—H17	119.7
H1A—C1—H1B	109.5	C18—C17—H17	119.7
N1—C1—H1C	109.5	C19—C18—C17	120.6 (2)
H1A—C1—H1C	109.5	C19—C18—H18	119.7
H1B—C1—H1C	109.5	C17—C18—H18	119.7
N1—C2—C3	101.37 (15)	C18—C19—C14	120.4 (2)
N1—C2—H2A	111.5	C18—C19—H19	119.8
C3—C2—H2A	111.5	C14—C19—H19	119.8
N1—C2—H2B	111.5	C36—C31—C32	116.1 (2)
C3—C2—H2B	111.5	C36—C31—C3	120.23 (19)
H2A—C2—H2B	109.3	C32—C31—C3	123.67 (19)
C2—C3—C31	116.15 (16)	C31—C32—C33	122.1 (2)
C2—C3—C4	103.51 (15)	C31—C32—H32	118.9
C31—C3—C4	116.98 (16)	C33—C32—H32	118.9
C2—C3—H3	106.5	C34—C33—C32	120.0 (2)
C31—C3—H3	106.5	C34—C33—H33	120.0
C4—C3—H3	106.5	C32—C33—H33	120.0
C41—C4—C45	106.83 (17)	C35—C34—C33	119.4 (2)
C41—C4—C3	112.00 (15)	C35—C34—Cl1	120.6 (2)
C45—C4—C3	111.62 (17)	C33—C34—Cl1	119.9 (2)
C41—C4—C5	112.83 (16)	C34—C35—C36	120.3 (3)
C45—C4—C5	110.64 (15)	C34—C35—H35	119.9
C3—C4—C5	103.02 (15)	C36—C35—H35	119.9
N1—C5—C6	109.41 (15)	C31—C36—C35	122.1 (2)
N1—C5—C12	114.58 (15)	C31—C36—H36	118.9
C6—C5—C12	100.23 (15)	C35—C36—H36	118.9
N1—C5—C4	102.88 (14)	N2—C41—C4	111.24 (16)
C6—C5—C4	116.86 (15)	N2—C41—H41A	109.4
C12—C5—C4	113.36 (15)	C4—C41—H41A	109.4
C11—C6—C7	120.10 (18)	N2—C41—H41B	109.4
C11—C6—C5	127.65 (19)	C4—C41—H41B	109.4
C7—C6—C5	112.17 (17)	H41A—C41—H41B	108.0
C8—C7—C6	120.7 (2)	N2—C42—H42A	109.5
C8—C7—C13	130.7 (2)	N2—C42—H42B	109.5
C6—C7—C13	108.46 (17)	H42A—C42—H42B	109.5
C9—C8—C7	118.7 (2)	N2—C42—H42C	109.5
C9—C8—H8	120.6	H42A—C42—H42C	109.5
C7—C8—H8	120.6	H42B—C42—H42C	109.5
C8—C9—C10	120.9 (2)	N2—C43—C44	110.7 (2)
C8—C9—H9	119.6	N2—C43—H43A	109.5
C10—C9—H9	119.6	C44—C43—H43A	109.5
C9—C10—C11	120.7 (2)	N2—C43—H43B	109.5
C9—C10—H10	119.6	C44—C43—H43B	109.5
C11—C10—H10	119.6	H43A—C43—H43B	108.1
C6—C11—C10	118.9 (2)	C45—C44—C43	113.6 (2)
C6—C11—H11	120.6	C45—C44—H44A	108.8
C10—C11—H11	120.6	C43—C44—H44A	108.8
N3—C12—C13	123.48 (19)	C45—C44—H44B	108.8
N3—C12—C5	125.84 (17)	C43—C44—H44B	108.8
C13—C12—C5	110.51 (16)	H44A—C44—H44B	107.7
N4—C13—C12	123.85 (18)	O1—C45—C44	121.4 (2)
N4—C13—C7	127.70 (18)	O1—C45—C4	121.9 (2)
C12—C13—C7	108.38 (18)	C44—C45—C4	116.6 (2)
N4—C14—C19	118.7 (2)	C2—N1—C1	116.20 (16)
N4—C14—C15	122.43 (19)	C2—N1—C5	107.75 (15)
C19—C14—C15	118.8 (2)	C1—N1—C5	115.92 (16)
N3—C15—C16	118.7 (2)	C43—N2—C41	108.79 (19)
N3—C15—C14	121.71 (18)	C43—N2—C42	111.5 (2)
C16—C15—C14	119.6 (2)	C41—N2—C42	110.65 (19)
C17—C16—C15	120.0 (2)	C12—N3—C15	114.47 (17)
C17—C16—H16	120.0	C13—N4—C14	113.86 (17)
C15—C16—H16	120.0

N1—C2—C3—C31	171.55 (16)	C14—C15—C16—C17	−1.1 (3)
N1—C2—C3—C4	41.92 (19)	C15—C16—C17—C18	−0.4 (4)
C2—C3—C4—C41	98.92 (19)	C16—C17—C18—C19	1.2 (4)
C31—C3—C4—C41	−30.2 (2)	C17—C18—C19—C14	−0.4 (4)
C2—C3—C4—C45	−141.35 (17)	N4—C14—C19—C18	178.0 (2)
C31—C3—C4—C45	89.5 (2)	C15—C14—C19—C18	−1.1 (3)
C2—C3—C4—C5	−22.61 (18)	C2—C3—C31—C36	158.8 (2)
C31—C3—C4—C5	−151.73 (16)	C4—C3—C31—C36	−78.4 (3)
C41—C4—C5—N1	−125.30 (16)	C2—C3—C31—C32	−18.6 (3)
C45—C4—C5—N1	115.08 (18)	C4—C3—C31—C32	104.2 (2)
C3—C4—C5—N1	−4.34 (18)	C36—C31—C32—C33	−0.1 (4)
C41—C4—C5—C6	114.83 (18)	C3—C31—C32—C33	177.4 (2)
C45—C4—C5—C6	−4.8 (2)	C31—C32—C33—C34	−0.4 (4)
C3—C4—C5—C6	−124.21 (17)	C32—C33—C34—C35	0.5 (4)
C41—C4—C5—C12	−1.0 (2)	C32—C33—C34—Cl1	−179.4 (2)
C45—C4—C5—C12	−120.61 (19)	C33—C34—C35—C36	−0.1 (5)
C3—C4—C5—C12	119.97 (16)	Cl1—C34—C35—C36	179.8 (3)
N1—C5—C6—C11	−51.1 (3)	C32—C31—C36—C35	0.4 (4)
C12—C5—C6—C11	−171.90 (19)	C3—C31—C36—C35	−177.1 (3)
C4—C5—C6—C11	65.2 (3)	C34—C35—C36—C31	−0.3 (5)
N1—C5—C6—C7	125.62 (18)	C45—C4—C41—N2	57.7 (2)
C12—C5—C6—C7	4.8 (2)	C3—C4—C41—N2	−179.81 (16)
C4—C5—C6—C7	−118.06 (19)	C5—C4—C41—N2	−64.1 (2)
C11—C6—C7—C8	−1.9 (3)	N2—C43—C44—C45	−47.8 (3)
C5—C6—C7—C8	−178.92 (18)	C43—C44—C45—O1	−139.5 (3)
C11—C6—C7—C13	173.82 (18)	C43—C44—C45—C4	40.4 (3)
C5—C6—C7—C13	−3.2 (2)	C41—C4—C45—O1	136.3 (2)
C6—C7—C8—C9	0.2 (3)	C3—C4—C45—O1	13.6 (3)
C13—C7—C8—C9	−174.4 (2)	C5—C4—C45—O1	−100.5 (2)
C7—C8—C9—C10	1.4 (4)	C41—C4—C45—C44	−43.6 (2)
C8—C9—C10—C11	−1.3 (4)	C3—C4—C45—C44	−166.30 (19)
C7—C6—C11—C10	2.0 (3)	C5—C4—C45—C44	79.6 (2)
C5—C6—C11—C10	178.47 (19)	C3—C2—N1—C1	−179.25 (17)
C9—C10—C11—C6	−0.4 (3)	C3—C2—N1—C5	−47.3 (2)
N1—C5—C12—N3	53.5 (3)	C6—C5—N1—C2	156.77 (16)
C6—C5—C12—N3	170.50 (18)	C12—C5—N1—C2	−91.62 (19)
C4—C5—C12—N3	−64.2 (2)	C4—C5—N1—C2	31.88 (19)
N1—C5—C12—C13	−121.80 (17)	C6—C5—N1—C1	−71.1 (2)
C6—C5—C12—C13	−4.8 (2)	C12—C5—N1—C1	40.5 (2)
C4—C5—C12—C13	120.51 (17)	C4—C5—N1—C1	164.01 (16)
N3—C12—C13—N4	5.1 (3)	C44—C43—N2—C41	62.2 (3)
C5—C12—C13—N4	−179.49 (18)	C44—C43—N2—C42	−175.5 (2)
N3—C12—C13—C7	−172.11 (18)	C4—C41—N2—C43	−69.7 (2)
C5—C12—C13—C7	3.3 (2)	C4—C41—N2—C42	167.5 (2)
C8—C7—C13—N4	−2.0 (4)	C13—C12—N3—C15	−3.6 (3)
C6—C7—C13—N4	−177.16 (19)	C5—C12—N3—C15	−178.36 (17)
C8—C7—C13—C12	175.1 (2)	C16—C15—N3—C12	−179.58 (18)
C6—C7—C13—C12	−0.1 (2)	C14—C15—N3—C12	−0.4 (3)
N4—C14—C15—N3	3.6 (3)	C12—C13—N4—C14	−1.7 (3)
C19—C14—C15—N3	−177.29 (19)	C7—C13—N4—C14	174.96 (18)
N4—C14—C15—C16	−177.21 (19)	C19—C14—N4—C13	178.54 (19)
C19—C14—C15—C16	1.9 (3)	C15—C14—N4—C13	−2.4 (3)
N3—C15—C16—C17	178.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41A···N3	0.97	2.39	2.988 (3)	120
C11—H11···Cg1ⁱ	0.93	2.89	3.655 (2)	140

Symmetry code: (i) x, −y, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41A···N3	0.97	2.39	2.988 (3)	119.6
C11—H11···Cg1ⁱ	0.93	2.89	3.655 (2)	140

Symmetry code: (i) x, −y, z−1/2.

Acknowledgements

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

References

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Volume 71| Part 2| February 2015| Pages o68-o69

doi:10.1107/S2056989014027698

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

Crystal structure of 1′,1′′-di­methyl-4′-(4-cholorophen­yl)di­spiro­[11H-indeno[1,2-b]quinoxaline-11,2′-pyrrolidine-3′,3′′-piperidin]-4′′-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1′,1′′-dimethyl-4′-(4-cholorophenyl)dispiro[11H-indeno[1,2-b]quinoxaline-11,2′-pyrrolidine-3′,3′′-piperidin]-4′′-one