5-Amino-6-benzoyl-8-nitro-2,3-di­hydro-1H-spiro­[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate

Nagalakshmi, R.A.; Suresh, J.; Sivakumar, S.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536814008800

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o604-o605

doi:10.1107/S1600536814008800

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5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate

R. A. Nagalakshmi,^a J. Suresh,^a S. Sivakumar,^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

(Received 11 March 2014; accepted 17 April 2014; online 26 April 2014)

In the title compound C₂₁H₁₇N₅O₄·C₂H₆OS, the central six-membered ring derived from 1,4-dihydropyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N atom [60 (2)°] indicate that these atoms are in sp² hybridization, leading to an essentially planar imidazolidine ring. The last heterocycle, an oxindole moiety, is also nearly planar with an r.m.s. deviation of 0.0185 (1) Å. The amine NH₂ group forms an intramolecular hydrogen bond with the benzoyl group, giving a S(6) motif. In the crystal, N—H⋯O hydrogen bonds lead to the formation of chains along the c-axis direction. Within the chains there are further N—H⋯O and C—H⋯O hydrogen bonds enclosing R²₂(14) ring motifs. The chains are linked via N—H⋯O and C—H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent molecule which acts as both an acceptor and a donor..

CCDC reference: 998123

Related literature

For a previous related work, see: Suresh et al. (2013 ). For conformational analysis of ring systems, and small rings fused to benzene, see: Cremer & Pople (1975 ); Allen (1981 ).

Experimental

Crystal data

C₂₁H₁₇N₅O₄·C₂H₆OS
M_r = 481.52
Monoclinic, P 2₁ /c
a = 16.476 (3) Å
b = 13.527 (2) Å
c = 10.0727 (18) Å
β = 99.868 (5)°
V = 2211.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.967, T_max = 0.974
31940 measured reflections
4109 independent reflections
2818 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.160
S = 1.05
4109 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O4	0.86	1.92	2.549 (3)	129
N2—H2A⋯O3ⁱ	0.86	2.30	2.939 (3)	131
N3—H3⋯O5ⁱⁱ	0.86	1.92	2.779 (4)	177
N5—H5⋯O3ⁱⁱⁱ	0.86	2.31	2.924 (3)	129
C6—H6B⋯O2ⁱⁱⁱ	0.97	2.59	3.274 (4)	128
C11—H11⋯O4ⁱ	0.93	2.43	3.346 (4)	167
C15—H15C⋯O2^iv	0.96	2.55	3.448 (4)	156
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) -x, -y+1, -z+1; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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

CCDC reference: 998123

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814008800/bh2496sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008800/bh2496Isup2.hkl

checkCIF report

Experimental top

Synthesis and crystallization top

A mixture of benzoylacetonitrile (1.0 mmol), isatin (1.0 mmol) and 2-(nitromethylene) imidazolidine was dissolved in 10 ml of EtOH, and triethylamine (1.0 mmol) was added. The reaction mixture was refluxed for 45 min. After completion of the reaction, as evident from TLC, the precipitated solid product was filtered and dried to obtain pure pale brown solid. Yield 94%. Melting point 530 K.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were placed in calculated positions and allowed to ride on their carrier atoms with C—H = 0.93 (aromatic CH), 0.96 (methyl CH₃) or 0.97 Å (methylene CH₂), and N—H = 0.86 Å. Isotropic displacement parameters for H atoms were calculated as U_iso = 1.5U_eq(C) for CH₃ groups and U_iso = 1.2U_eq(carrier atom) for all other H atoms.

Results and discussion top

Our interest in preparing pharmacologically active pyridine-related compounds (Suresh et al., 2013) led us to the title compound, derived from a 1,4-dihydropyridine, and we have undertaken X-ray crystal structure determination of this compound in order to establish its molecular conformation.

In the title compound (Fig. 1), the central pyridine ring adopts a skew-boat conformation with the puckering parameters Q = 0.127 (3) Å, θ = 87.3 (13) and ϕ = 198.3 (3)° (Cremer & Pople, 1975). The sums of bond angles around N4 and N5, 358.7 (2)° and 360 (2)° respectively, show that N atoms are in sp² hybridization, leading to an essentially planar imidazolidine ring. The C2/C8/N3/C9/C10 ring of the oxindole moiety is planar with r.m.s. deviation of 0.0185 (1) Å. The small tilt between the planes of the five and six-membered rings in the oxindole unit is 1.21 (1)°. The sum of the bond angles around N3 atom is 360 (1)° implying a noticeable flattening of the geometry about N3. The shorter bond lengths N3—C8 = 1.337 (4) Å and N3—C9 = 1.401 (4) Å indicate the electron donating effect of the N atom. The nitro group, N1/O1/O2, is twisted away from the mean plane of the six-membered ring, forming the dihedral angle of 8.90 (1)°. In the benzene ring (C9···C14) of the oxindole ring system, the expansion of the ipso angles at C9, C12 and C13 [121.9 (3), 120.8 (3) and 121.3 (3)°, respectively] and the contraction of the apical angles at C10, C11 and C14 [120.5 (3), 118.1 (3) and 117.3 (3)°, respectively] are caused by the fusion of the smaller ring to the six-membered benzene ring, and the strain is taken up by the angular distortion rather than by bond length distortions (Allen, 1981). The short contacts H2A···H7A (2.17 Å) and H2A···H7B (2.31 Å) result in the substantial widening of angle C7—N4—C4 to 124.9 (2)°.

The crystal structure features weak intra-molecular N—H···O interactions and N—H···O and C—H···O inter-molecular interactions. An inter-molecular N2—H2A···O3 interaction forms a chain along the c axis, while inter-molecular N5—H5···O3 and C6—H6B···O2 interactions form ring motifs R₂²(14). The solvent molecule, dimetyl sulfoxide, also takes part in the N—H···O and in the C—H···O inter-molecular interactions (Fig. 2).

Related literature top

For a previous related work, see: Suresh et al. (2013). For conformational analysis of ring systems, and small rings fused to benzene, see: Cremer & Pople (1975); Allen (1981).

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 the title compound, showing 20% probability displacement ellipsoids. All H atoms are omitted for clarity.
	Fig. 2. Partial packing diagram of the title compound. Dashed bonds represent inter-molecular hydrogen bonds.

(I) top

Crystal data top

C₂₁H₁₇N₅O₄·C₂H₆OS	F(000) = 1008
M_r = 481.52	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 530 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.476 (3) Å	Cell parameters from 2000 reflections
b = 13.527 (2) Å	θ = 2–31°
c = 10.0727 (18) Å	µ = 0.19 mm⁻¹
β = 99.868 (5)°	T = 293 K
V = 2211.7 (7) Å³	Block, brown
Z = 4	0.21 × 0.19 × 0.18 mm

Data collection top

Bruker Kappa APEXII diffractometer	4109 independent reflections
Radiation source: fine-focus sealed tube	2818 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 0 pixels mm^-1	θ_max = 25.5°, θ_min = 2.5°
ω and ϕ scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −16→16
T_min = 0.967, T_max = 0.974	l = −12→12
31940 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0634P)² + 2.4142P] where P = (F_o² + 2F_c²)/3
4109 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.92 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³
0 constraints

Crystal data top

C₂₁H₁₇N₅O₄·C₂H₆OS	V = 2211.7 (7) Å³
M_r = 481.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.476 (3) Å	µ = 0.19 mm⁻¹
b = 13.527 (2) Å	T = 293 K
c = 10.0727 (18) Å	0.21 × 0.19 × 0.18 mm
β = 99.868 (5)°

Data collection top

Bruker Kappa APEXII diffractometer	4109 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2818 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.070
31940 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.05	Δρ_max = 0.92 e Å⁻³
4109 reflections	Δρ_min = −0.47 e Å⁻³
307 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.12735 (16)	0.47401 (19)	0.4943 (3)	0.0273 (6)
C2	0.19857 (15)	0.4409 (2)	0.6005 (3)	0.0268 (6)
C3	0.20085 (16)	0.3272 (2)	0.6119 (3)	0.0285 (6)
C4	0.14829 (16)	0.2694 (2)	0.5220 (3)	0.0292 (6)
C5	0.08157 (16)	0.4092 (2)	0.4049 (3)	0.0292 (6)
C6	−0.01200 (18)	0.3357 (2)	0.2370 (3)	0.0429 (8)
H6A	−0.0032	0.3343	0.1442	0.051*
H6B	−0.0705	0.3291	0.2384	0.051*
C7	0.03642 (18)	0.2551 (2)	0.3186 (3)	0.0432 (8)
H7A	0.0010	0.2147	0.3641	0.052*
H7B	0.0641	0.2132	0.2622	0.052*
C8	0.18947 (16)	0.4842 (2)	0.7405 (3)	0.0293 (6)
C9	0.30975 (16)	0.5444 (2)	0.6929 (3)	0.0330 (7)
C10	0.27937 (15)	0.4874 (2)	0.5812 (3)	0.0295 (6)
C11	0.32187 (17)	0.4803 (2)	0.4754 (3)	0.0371 (7)
H11	0.3022	0.4414	0.4006	0.045*
C12	0.39483 (19)	0.5327 (2)	0.4833 (4)	0.0473 (8)
H12	0.4244	0.5293	0.4127	0.057*
C13	0.42409 (19)	0.5898 (3)	0.5948 (4)	0.0494 (9)
H13	0.4731	0.6246	0.5978	0.059*
C14	0.38202 (18)	0.5964 (2)	0.7022 (4)	0.0434 (8)
H14	0.4019	0.6346	0.7775	0.052*
C15	0.2595 (3)	0.6930 (3)	0.2703 (4)	0.0615 (10)
H15A	0.3158	0.6979	0.3147	0.092*
H15B	0.2246	0.6827	0.3362	0.092*
H15C	0.2439	0.7531	0.2218	0.092*
C16	0.1423 (2)	0.6058 (3)	0.0959 (4)	0.0730 (12)
H16A	0.1245	0.5554	0.0302	0.109*
H16B	0.1319	0.6697	0.0550	0.109*
H16C	0.1126	0.5995	0.1695	0.109*
C31	0.25828 (18)	0.2769 (2)	0.7134 (3)	0.0362 (7)
C32	0.33727 (18)	0.3217 (2)	0.7853 (3)	0.0363 (7)
C33	0.4043 (2)	0.3233 (3)	0.7190 (4)	0.0495 (9)
H33	0.3980	0.3065	0.6283	0.059*
C34	0.4805 (2)	0.3501 (3)	0.7889 (5)	0.0672 (12)
H34	0.5259	0.3500	0.7453	0.081*
C35	0.4901 (3)	0.3769 (3)	0.9213 (5)	0.0768 (14)
H35	0.5418	0.3951	0.9672	0.092*
C36	0.4236 (3)	0.3768 (3)	0.9867 (4)	0.0719 (13)
H36	0.4299	0.3968	1.0763	0.086*
C37	0.3472 (2)	0.3471 (3)	0.9197 (3)	0.0519 (9)
H37	0.3027	0.3443	0.9651	0.062*
N1	0.10891 (14)	0.57350 (18)	0.4841 (2)	0.0330 (6)
N2	0.14345 (15)	0.17067 (18)	0.5281 (3)	0.0398 (6)
H2A	0.1097	0.1391	0.4684	0.048*
H2B	0.1741	0.1389	0.5917	0.048*
N3	0.25616 (14)	0.53850 (17)	0.7866 (2)	0.0342 (6)
H3	0.2651	0.5665	0.8644	0.041*
N4	0.09609 (13)	0.31051 (18)	0.4158 (2)	0.0326 (6)
N5	0.02048 (14)	0.42620 (19)	0.3037 (2)	0.0374 (6)
H5	0.0021	0.4842	0.2801	0.045*
O1	0.05174 (13)	0.60506 (16)	0.3938 (2)	0.0445 (6)
O2	0.14848 (13)	0.63220 (15)	0.5658 (2)	0.0431 (6)
O3	0.13161 (12)	0.46735 (14)	0.80020 (19)	0.0352 (5)
O4	0.24819 (17)	0.18945 (18)	0.7443 (3)	0.0682 (8)
O5	0.28997 (18)	0.6227 (3)	0.0417 (3)	0.0927 (12)
S1	0.24911 (7)	0.59246 (8)	0.15647 (10)	0.0650 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0223 (13)	0.0279 (15)	0.0298 (14)	0.0015 (11)	−0.0003 (11)	0.0011 (12)
C2	0.0203 (13)	0.0296 (14)	0.0287 (14)	−0.0009 (11)	−0.0009 (11)	−0.0003 (12)
C3	0.0221 (13)	0.0311 (15)	0.0312 (15)	−0.0011 (11)	0.0015 (11)	−0.0002 (12)
C4	0.0213 (13)	0.0322 (16)	0.0343 (15)	−0.0013 (11)	0.0048 (11)	−0.0007 (12)
C5	0.0209 (13)	0.0380 (17)	0.0283 (14)	0.0006 (11)	0.0034 (11)	0.0006 (12)
C6	0.0273 (16)	0.057 (2)	0.0399 (17)	0.0011 (14)	−0.0074 (13)	−0.0116 (15)
C7	0.0305 (16)	0.0461 (19)	0.0474 (19)	−0.0066 (14)	−0.0093 (14)	−0.0115 (15)
C8	0.0247 (14)	0.0260 (14)	0.0352 (15)	0.0037 (11)	−0.0007 (12)	0.0025 (12)
C9	0.0234 (14)	0.0331 (16)	0.0404 (16)	0.0002 (12)	−0.0006 (12)	−0.0012 (13)
C10	0.0192 (13)	0.0307 (15)	0.0366 (15)	0.0018 (11)	−0.0009 (11)	0.0020 (12)
C11	0.0277 (15)	0.0436 (18)	0.0385 (17)	0.0032 (13)	0.0015 (12)	0.0028 (14)
C12	0.0321 (17)	0.054 (2)	0.058 (2)	−0.0006 (15)	0.0134 (15)	0.0095 (17)
C13	0.0248 (16)	0.050 (2)	0.073 (2)	−0.0077 (14)	0.0066 (16)	0.0033 (18)
C14	0.0257 (15)	0.0425 (19)	0.058 (2)	−0.0073 (13)	−0.0031 (14)	−0.0093 (16)
C15	0.074 (3)	0.059 (2)	0.049 (2)	0.005 (2)	0.0023 (19)	−0.0067 (18)
C16	0.059 (3)	0.089 (3)	0.071 (3)	−0.006 (2)	0.012 (2)	−0.018 (2)
C31	0.0331 (16)	0.0346 (17)	0.0383 (17)	0.0008 (13)	−0.0012 (13)	0.0013 (13)
C32	0.0307 (16)	0.0320 (16)	0.0423 (17)	0.0042 (12)	−0.0049 (13)	0.0066 (13)
C33	0.0407 (19)	0.050 (2)	0.058 (2)	0.0070 (15)	0.0094 (16)	0.0066 (17)
C34	0.0297 (19)	0.068 (3)	0.103 (4)	0.0031 (18)	0.007 (2)	0.021 (2)
C35	0.042 (2)	0.081 (3)	0.095 (3)	−0.020 (2)	−0.024 (2)	0.028 (3)
C36	0.073 (3)	0.081 (3)	0.050 (2)	−0.023 (2)	−0.021 (2)	0.009 (2)
C37	0.047 (2)	0.064 (2)	0.0402 (19)	−0.0104 (17)	−0.0042 (15)	0.0026 (17)
N1	0.0254 (12)	0.0367 (14)	0.0352 (13)	0.0021 (10)	0.0006 (10)	0.0050 (11)
N2	0.0381 (14)	0.0295 (14)	0.0482 (15)	−0.0054 (11)	−0.0028 (12)	−0.0016 (11)
N3	0.0299 (13)	0.0379 (14)	0.0322 (13)	−0.0008 (10)	−0.0019 (10)	−0.0067 (11)
N4	0.0218 (12)	0.0362 (14)	0.0364 (13)	0.0002 (10)	−0.0045 (10)	−0.0058 (11)
N5	0.0274 (13)	0.0447 (15)	0.0355 (13)	0.0032 (11)	−0.0080 (10)	−0.0004 (12)
O1	0.0371 (12)	0.0430 (13)	0.0466 (13)	0.0088 (10)	−0.0117 (10)	0.0091 (10)
O2	0.0402 (12)	0.0334 (12)	0.0500 (13)	−0.0012 (9)	−0.0083 (10)	−0.0052 (10)
O3	0.0287 (11)	0.0408 (12)	0.0360 (11)	0.0024 (9)	0.0054 (9)	0.0033 (9)
O4	0.0734 (18)	0.0428 (15)	0.0733 (18)	−0.0118 (13)	−0.0298 (14)	0.0201 (13)
O5	0.0581 (18)	0.163 (3)	0.0610 (17)	−0.0245 (19)	0.0210 (14)	−0.053 (2)
S1	0.0735 (7)	0.0610 (7)	0.0544 (6)	0.0189 (5)	−0.0064 (5)	−0.0117 (5)

Geometric parameters (Å, º) top

C1—N1	1.380 (4)	C13—H13	0.9300
C1—C5	1.384 (4)	C14—H14	0.9300
C1—C2	1.514 (3)	C15—S1	1.769 (4)
C2—C10	1.515 (4)	C15—H15A	0.9600
C2—C3	1.542 (4)	C15—H15B	0.9600
C2—C8	1.558 (4)	C15—H15C	0.9600
C3—C4	1.383 (4)	C16—S1	1.771 (4)
C3—C31	1.439 (4)	C16—H16A	0.9600
C4—N2	1.340 (4)	C16—H16B	0.9600
C4—N4	1.370 (3)	C16—H16C	0.9600
C5—N5	1.324 (3)	C31—O4	1.242 (4)
C5—N4	1.357 (4)	C31—C32	1.504 (4)
C6—N5	1.454 (4)	C32—C37	1.380 (5)
C6—C7	1.509 (4)	C32—C33	1.385 (4)
C6—H6A	0.9700	C33—C34	1.379 (5)
C6—H6B	0.9700	C33—H33	0.9300
C7—N4	1.468 (3)	C34—C35	1.364 (6)
C7—H7A	0.9700	C34—H34	0.9300
C7—H7B	0.9700	C35—C36	1.372 (6)
C8—O3	1.232 (3)	C35—H35	0.9300
C8—N3	1.337 (4)	C36—C37	1.382 (5)
C9—C14	1.373 (4)	C36—H36	0.9300
C9—C10	1.385 (4)	C37—H37	0.9300
C9—N3	1.401 (4)	N1—O2	1.245 (3)
C10—C11	1.375 (4)	N1—O1	1.266 (3)
C11—C12	1.386 (4)	N2—H2A	0.8600
C11—H11	0.9300	N2—H2B	0.8600
C12—C13	1.380 (5)	N3—H3	0.8600
C12—H12	0.9300	N5—H5	0.8600
C13—C14	1.384 (5)	O5—S1	1.491 (3)

N1—C1—C5	118.8 (2)	S1—C15—H15A	109.5
N1—C1—C2	118.4 (2)	S1—C15—H15B	109.5
C5—C1—C2	122.8 (2)	H15A—C15—H15B	109.5
C1—C2—C10	112.2 (2)	S1—C15—H15C	109.5
C1—C2—C3	110.7 (2)	H15A—C15—H15C	109.5
C10—C2—C3	114.4 (2)	H15B—C15—H15C	109.5
C1—C2—C8	110.2 (2)	S1—C16—H16A	109.5
C10—C2—C8	100.5 (2)	S1—C16—H16B	109.5
C3—C2—C8	108.2 (2)	H16A—C16—H16B	109.5
C4—C3—C31	117.4 (3)	S1—C16—H16C	109.5
C4—C3—C2	120.7 (2)	H16A—C16—H16C	109.5
C31—C3—C2	121.9 (2)	H16B—C16—H16C	109.5
N2—C4—N4	114.0 (2)	O4—C31—C3	121.9 (3)
N2—C4—C3	124.7 (3)	O4—C31—C32	113.9 (3)
N4—C4—C3	121.4 (2)	C3—C31—C32	124.1 (3)
N5—C5—N4	109.5 (2)	C37—C32—C33	119.9 (3)
N5—C5—C1	130.4 (3)	C37—C32—C31	121.4 (3)
N4—C5—C1	120.1 (2)	C33—C32—C31	118.1 (3)
N5—C6—C7	103.8 (2)	C34—C33—C32	119.3 (4)
N5—C6—H6A	111.0	C34—C33—H33	120.3
C7—C6—H6A	111.0	C32—C33—H33	120.3
N5—C6—H6B	111.0	C35—C34—C33	120.8 (4)
C7—C6—H6B	111.0	C35—C34—H34	119.6
H6A—C6—H6B	109.0	C33—C34—H34	119.6
N4—C7—C6	103.1 (2)	C34—C35—C36	120.1 (4)
N4—C7—H7A	111.2	C34—C35—H35	120.0
C6—C7—H7A	111.2	C36—C35—H35	120.0
N4—C7—H7B	111.2	C35—C36—C37	120.1 (4)
C6—C7—H7B	111.2	C35—C36—H36	120.0
H7A—C7—H7B	109.1	C37—C36—H36	120.0
O3—C8—N3	126.2 (3)	C32—C37—C36	119.8 (4)
O3—C8—C2	125.1 (2)	C32—C37—H37	120.1
N3—C8—C2	108.7 (2)	C36—C37—H37	120.1
C14—C9—C10	121.9 (3)	O2—N1—O1	120.1 (2)
C14—C9—N3	128.6 (3)	O2—N1—C1	119.3 (2)
C10—C9—N3	109.5 (2)	O1—N1—C1	120.6 (2)
C11—C10—C9	120.5 (3)	C4—N2—H2A	120.0
C11—C10—C2	130.2 (3)	C4—N2—H2B	120.0
C9—C10—C2	109.3 (2)	H2A—N2—H2B	120.0
C10—C11—C12	118.1 (3)	C8—N3—C9	111.9 (2)
C10—C11—H11	120.9	C8—N3—H3	124.1
C12—C11—H11	120.9	C9—N3—H3	124.1
C13—C12—C11	120.8 (3)	C5—N4—C4	122.7 (2)
C13—C12—H12	119.6	C5—N4—C7	111.1 (2)
C11—C12—H12	119.6	C4—N4—C7	124.9 (2)
C12—C13—C14	121.3 (3)	C5—N5—C6	112.4 (2)
C12—C13—H13	119.3	C5—N5—H5	123.8
C14—C13—H13	119.3	C6—N5—H5	123.8
C9—C14—C13	117.3 (3)	O5—S1—C15	106.5 (2)
C9—C14—H14	121.3	O5—S1—C16	105.0 (2)
C13—C14—H14	121.3	C15—S1—C16	97.2 (2)

N1—C1—C2—C10	−60.0 (3)	C10—C9—C14—C13	−0.1 (5)
C5—C1—C2—C10	118.2 (3)	N3—C9—C14—C13	179.9 (3)
N1—C1—C2—C3	170.8 (2)	C12—C13—C14—C9	−0.4 (5)
C5—C1—C2—C3	−10.9 (4)	C4—C3—C31—O4	−18.9 (5)
N1—C1—C2—C8	51.1 (3)	C2—C3—C31—O4	162.4 (3)
C5—C1—C2—C8	−130.6 (3)	C4—C3—C31—C32	157.3 (3)
C1—C2—C3—C4	6.8 (4)	C2—C3—C31—C32	−21.4 (4)
C10—C2—C3—C4	−121.2 (3)	O4—C31—C32—C37	−73.6 (4)
C8—C2—C3—C4	127.7 (3)	C3—C31—C32—C37	109.9 (4)
C1—C2—C3—C31	−174.6 (2)	O4—C31—C32—C33	96.9 (4)
C10—C2—C3—C31	57.4 (3)	C3—C31—C32—C33	−79.6 (4)
C8—C2—C3—C31	−53.7 (3)	C37—C32—C33—C34	0.2 (5)
C31—C3—C4—N2	4.5 (4)	C31—C32—C33—C34	−170.4 (3)
C2—C3—C4—N2	−176.8 (3)	C32—C33—C34—C35	−1.3 (6)
C31—C3—C4—N4	−174.9 (3)	C33—C34—C35—C36	0.3 (6)
C2—C3—C4—N4	3.8 (4)	C34—C35—C36—C37	1.8 (7)
N1—C1—C5—N5	1.4 (5)	C33—C32—C37—C36	1.9 (5)
C2—C1—C5—N5	−176.8 (3)	C31—C32—C37—C36	172.2 (3)
N1—C1—C5—N4	−177.4 (2)	C35—C36—C37—C32	−2.8 (6)
C2—C1—C5—N4	4.4 (4)	C5—C1—N1—O2	178.4 (2)
N5—C6—C7—N4	−4.7 (3)	C2—C1—N1—O2	−3.3 (4)
C1—C2—C8—O3	61.2 (3)	C5—C1—N1—O1	−0.7 (4)
C10—C2—C8—O3	179.8 (3)	C2—C1—N1—O1	177.6 (2)
C3—C2—C8—O3	−60.0 (3)	O3—C8—N3—C9	−179.0 (3)
C1—C2—C8—N3	−121.4 (2)	C2—C8—N3—C9	3.6 (3)
C10—C2—C8—N3	−2.8 (3)	C14—C9—N3—C8	177.1 (3)
C3—C2—C8—N3	117.4 (2)	C10—C9—N3—C8	−2.9 (3)
C14—C9—C10—C11	0.8 (4)	N5—C5—N4—C4	−171.2 (2)
N3—C9—C10—C11	−179.2 (2)	C1—C5—N4—C4	7.8 (4)
C14—C9—C10—C2	−179.2 (3)	N5—C5—N4—C7	−3.7 (3)
N3—C9—C10—C2	0.9 (3)	C1—C5—N4—C7	175.3 (3)
C1—C2—C10—C11	−61.7 (4)	N2—C4—N4—C5	168.5 (3)
C3—C2—C10—C11	65.5 (4)	C3—C4—N4—C5	−12.0 (4)
C8—C2—C10—C11	−178.8 (3)	N2—C4—N4—C7	2.8 (4)
C1—C2—C10—C9	118.2 (3)	C3—C4—N4—C7	−177.8 (3)
C3—C2—C10—C9	−114.6 (3)	C6—C7—N4—C5	5.3 (3)
C8—C2—C10—C9	1.1 (3)	C6—C7—N4—C4	172.5 (3)
C9—C10—C11—C12	−0.9 (4)	N4—C5—N5—C6	0.3 (3)
C2—C10—C11—C12	179.0 (3)	C1—C5—N5—C6	−178.6 (3)
C10—C11—C12—C13	0.4 (5)	C7—C6—N5—C5	3.0 (3)
C11—C12—C13—C14	0.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O4	0.86	1.92	2.549 (3)	129
N2—H2A···O3ⁱ	0.86	2.30	2.939 (3)	131
N3—H3···O5ⁱⁱ	0.86	1.92	2.779 (4)	177
N5—H5···O1	0.86	2.08	2.604 (3)	119
N5—H5···O3ⁱⁱⁱ	0.86	2.31	2.924 (3)	129
C6—H6B···O2ⁱⁱⁱ	0.97	2.59	3.274 (4)	128
C11—H11···O4ⁱ	0.93	2.43	3.346 (4)	167
C15—H15C···O2^iv	0.96	2.55	3.448 (4)	156

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y, z+1; (iii) −x, −y+1, −z+1; (iv) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O4	0.86	1.92	2.549 (3)	129.1
N2—H2A···O3ⁱ	0.86	2.30	2.939 (3)	131.4
N3—H3···O5ⁱⁱ	0.86	1.92	2.779 (4)	176.5
N5—H5···O3ⁱⁱⁱ	0.86	2.31	2.924 (3)	128.7
C6—H6B···O2ⁱⁱⁱ	0.97	2.59	3.274 (4)	128.2
C11—H11···O4ⁱ	0.93	2.43	3.346 (4)	166.7
C15—H15C···O2^iv	0.96	2.55	3.448 (4)	155.8

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y, z+1; (iii) −x, −y+1, −z+1; (iv) x, −y+3/2, 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 the fast-track scheme (No. SR/FT/CS-073/2009).

References

Allen, F. H. (1981). Acta Cryst. B37, 900–906. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science 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
Suresh, J., Nagalakshmi, R. A., Sivakumar, S., Kumar, R. R. & Lakshman, P. L. N. (2013). Acta Cryst. E69, o256–o257. CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 5| May 2014| Pages o604-o605

doi:10.1107/S1600536814008800

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

5-Amino-6-benzoyl-8-nitro-2,3-di­hydro-1H-spiro­[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one di­methyl sulfoxide monosolvate

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Experimental

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organic compounds

5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate