3′-(4-Chloro­benzo­yl)-4′-(4-chloro­phen­yl)-1′-methyl­spiro­[indoline-3,2′-pyrrolidin]-2-one

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

doi:10.1107/S1600536811044618

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3128

doi:10.1107/S1600536811044618

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3′-(4-Chlorobenzoyl)-4′-(4-chlorophenyl)-1′-methylspiro[indoline-3,2′-pyrrolidin]-2-one

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 24 October 2011; accepted 25 October 2011; online 29 October 2011)

In the title compound, C₂₅H₂₀Cl₂N₂O₂, the pyrrolidine ring adopts an envelope conformation and the best plane through the five ring atoms makes a dihedral angle of 87.03 (8)° with the indoline ring. Molecules are connected by pairs of N—H⋯O hydrogen bonds into centrosymmetric dimers with an R₂²(8) graph-set ring motif. C—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For substituted pyrrolidine compounds, see: Coldham & Hufton (2005 ). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₅H₂₀Cl₂N₂O₂
M_r = 451.33
Monoclinic, P 2₁ /c
a = 11.4139 (2) Å
b = 11.6957 (2) Å
c = 16.5262 (2) Å
β = 102.037 (1)°
V = 2157.64 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
20528 measured reflections
5426 independent reflections
3812 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.03
5426 reflections
293 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.85 (2)	2.06 (2)	2.876 (2)	160
C24—H24⋯O1ⁱⁱ	0.93	2.42	3.104 (2)	130
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044618/bt5687sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044618/bt5687Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044618/bt5687Isup3.cml

checkCIF report

Comment top

Substituted pyrrolidine compounds are an important class of heterocyclic compounds with wide spread applications to the synthesis of biologically active compounds and natural products (Coldham & Hufton, 2005).

The indoline ring is essentially planar with a maximum deviation of 0.0594 (16)Å for atom C12. The oxygen atom O2 deviates with the value of 0.0566 (13)Å from the indoline ring. The phenyl ring of chlorophenyl group makes a dihedral angle of 79.68 (9)° and 20.47 (7)° with the pyrollidin ring and indoline ring system. The phenyl ring of chlorobenzaldehyde group makes a dihedral angle of 71.39 (9)° and 35.17 (8)° with the pyrrolidin ring and indoline ring system, respectively.

The pyrrolidin ring adopts an envelope conformation. The pyrrolidin ring makes a dihedral angle of 87.03 (8)° with the indoline ring system. The crystal structure is stabilized by C—H···O and N—H···O hydrogen bonds resulting in R²₂(16) and R²₂(8) graph-set ring motifs (Bernstein et al., 1995).

Related literature top

For substituted pyrrolidine compounds, see: Coldham & Hufton (2005). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

A solution of (E)-1,3-bis(4-chlorophenyl)prop-2-en-1-one(2 mmol), isatin (1 eq.) and sarcosine( 1 eq.) was refluxed in dry toluene for 8 hrs at 110°C using Dean-Stark apparatus.After the completion of reaction as indicated by TLC,toluene was evaporated under reduced pressure.The crude product was purified by column chromatography using hexane: EtOAc (8:2) as eluent.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (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 b axis, showing the hydrogen bonds resulting in R²₂(16) and R²₂(8) graph-set ring motifs; H-atoms not involved in H-bonds have been excluded for clarity.

3'-(4-Chlorobenzoyl)-4'-(4-chlorophenyl)-1'-methylspiro[indoline-3,2'- pyrrolidin]-2-one top

Crystal data top

C₂₅H₂₀Cl₂N₂O₂	F(000) = 936
M_r = 451.33	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5426 reflections
a = 11.4139 (2) Å	θ = 1.8–28.4°
b = 11.6957 (2) Å	µ = 0.33 mm⁻¹
c = 16.5262 (2) Å	T = 293 K
β = 102.037 (1)°	Block, colourless
V = 2157.64 (6) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	3812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 28.4°, θ_min = 1.8°
ω and ϕ scans	h = −15→13
20528 measured reflections	k = −15→15
5426 independent reflections	l = −22→22

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0497P)² + 0.5071P] where P = (F_o² + 2F_c²)/3
5426 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₅H₂₀Cl₂N₂O₂	V = 2157.64 (6) Å³
M_r = 451.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4139 (2) Å	µ = 0.33 mm⁻¹
b = 11.6957 (2) Å	T = 293 K
c = 16.5262 (2) Å	0.20 × 0.20 × 0.20 mm
β = 102.037 (1)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	3812 reflections with I > 2σ(I)
20528 measured reflections	R_int = 0.026
5426 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.33 e Å⁻³
5426 reflections	Δρ_min = −0.44 e Å⁻³
293 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
Cl1	−0.14204 (5)	0.56050 (5)	0.16763 (3)	0.06775 (17)
Cl2	0.85262 (5)	0.60950 (6)	0.62529 (4)	0.0862 (2)
C9	0.11880 (14)	0.73473 (15)	0.50025 (9)	0.0400 (4)
N2	0.48172 (13)	0.92400 (12)	0.60195 (9)	0.0433 (3)
C15	0.37099 (14)	0.80302 (13)	0.66407 (8)	0.0367 (3)
C7	0.31713 (14)	0.62491 (14)	0.54566 (9)	0.0394 (3)
O2	0.34978 (11)	0.96763 (11)	0.48075 (8)	0.0564 (3)
N1	0.17789 (11)	0.88494 (12)	0.59138 (8)	0.0420 (3)
C8	0.25585 (13)	0.73727 (14)	0.51710 (9)	0.0359 (3)
C12	0.29245 (13)	0.83649 (13)	0.58229 (8)	0.0350 (3)
C20	0.05641 (13)	0.69085 (15)	0.41599 (9)	0.0407 (4)
C23	−0.06461 (15)	0.61146 (16)	0.26300 (10)	0.0472 (4)
O1	0.25970 (12)	0.54417 (11)	0.56163 (9)	0.0602 (3)
C4	0.45034 (14)	0.61803 (13)	0.55866 (9)	0.0381 (3)
C13	0.37572 (14)	0.91885 (14)	0.54743 (9)	0.0396 (3)
C14	0.48245 (14)	0.85308 (14)	0.67070 (9)	0.0402 (3)
C10	0.08849 (14)	0.85794 (16)	0.51710 (10)	0.0457 (4)
H10A	0.0963	0.9076	0.4715	0.055*
H10B	0.0079	0.8643	0.5270	0.055*
C5	0.51767 (14)	0.68787 (15)	0.51797 (9)	0.0429 (4)
H5	0.4790	0.7376	0.4771	0.052*
C25	−0.04115 (14)	0.61909 (16)	0.40920 (10)	0.0459 (4)
H25	−0.0664	0.5969	0.4568	0.055*
C1	0.69779 (16)	0.61090 (17)	0.59772 (11)	0.0533 (4)
C24	−0.10233 (15)	0.57939 (16)	0.33323 (10)	0.0484 (4)
H24	−0.1682	0.5315	0.3298	0.058*
C6	0.64165 (15)	0.68453 (17)	0.53744 (11)	0.0506 (4)
H6	0.6862	0.7316	0.5100	0.061*
C22	0.03220 (16)	0.68206 (19)	0.26713 (10)	0.0593 (5)
H22	0.0576	0.7029	0.2193	0.071*
C16	0.34817 (17)	0.73153 (15)	0.72517 (9)	0.0465 (4)
H16	0.2726	0.6999	0.7218	0.056*
C2	0.63333 (18)	0.53729 (17)	0.63664 (11)	0.0570 (5)
H2	0.6726	0.4854	0.6757	0.068*
C17	0.4410 (2)	0.70793 (18)	0.79193 (10)	0.0600 (5)
H17	0.4278	0.6597	0.8339	0.072*
C3	0.50996 (17)	0.54119 (15)	0.61720 (10)	0.0500 (4)
H3	0.4661	0.4918	0.6436	0.060*
C21	0.09178 (16)	0.72204 (18)	0.34360 (10)	0.0563 (5)
H21	0.1569	0.7708	0.3465	0.068*
C19	0.57585 (17)	0.82942 (18)	0.73636 (10)	0.0556 (5)
H19	0.6512	0.8619	0.7400	0.067*
C18	0.5529 (2)	0.75563 (19)	0.79644 (11)	0.0658 (6)
H18	0.6143	0.7376	0.8411	0.079*
C11	0.18210 (18)	1.00343 (17)	0.61905 (12)	0.0593 (5)
H11A	0.1973	1.0524	0.5758	0.089*
H11B	0.2450	1.0123	0.6672	0.089*
H11C	0.1068	1.0236	0.6324	0.089*
H2A	0.5428 (19)	0.9548 (17)	0.5892 (12)	0.059 (6)*
H8	0.2804 (14)	0.7597 (13)	0.4670 (10)	0.037 (4)*
H9	0.0928 (14)	0.6848 (14)	0.5430 (10)	0.039 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0563 (3)	0.0957 (4)	0.0465 (2)	−0.0108 (3)	0.0000 (2)	−0.0216 (2)
Cl2	0.0442 (3)	0.1103 (5)	0.0945 (4)	0.0194 (3)	−0.0074 (3)	−0.0141 (4)
C9	0.0320 (8)	0.0555 (10)	0.0323 (7)	−0.0082 (7)	0.0064 (6)	0.0019 (7)
N2	0.0359 (7)	0.0450 (8)	0.0466 (7)	−0.0103 (6)	0.0036 (6)	0.0004 (6)
C15	0.0392 (8)	0.0399 (8)	0.0291 (6)	0.0034 (7)	0.0031 (6)	−0.0034 (6)
C7	0.0436 (9)	0.0440 (9)	0.0317 (7)	−0.0064 (7)	0.0103 (6)	−0.0045 (6)
O2	0.0453 (7)	0.0658 (8)	0.0553 (7)	−0.0057 (6)	0.0045 (6)	0.0267 (6)
N1	0.0338 (7)	0.0526 (8)	0.0384 (7)	0.0027 (6)	0.0051 (5)	−0.0035 (6)
C8	0.0311 (7)	0.0481 (9)	0.0286 (6)	−0.0063 (6)	0.0061 (6)	0.0009 (6)
C12	0.0321 (8)	0.0400 (8)	0.0323 (7)	−0.0030 (6)	0.0052 (6)	0.0020 (6)
C20	0.0323 (8)	0.0534 (9)	0.0351 (7)	−0.0051 (7)	0.0042 (6)	0.0016 (7)
C23	0.0367 (9)	0.0630 (11)	0.0385 (8)	−0.0009 (8)	−0.0002 (7)	−0.0070 (8)
O1	0.0583 (8)	0.0485 (7)	0.0773 (9)	−0.0123 (6)	0.0220 (7)	0.0039 (6)
C4	0.0425 (9)	0.0401 (8)	0.0315 (7)	0.0011 (7)	0.0072 (6)	−0.0053 (6)
C13	0.0355 (8)	0.0408 (8)	0.0416 (8)	−0.0027 (7)	0.0057 (6)	0.0040 (6)
C14	0.0388 (8)	0.0441 (9)	0.0353 (7)	0.0022 (7)	0.0022 (6)	−0.0070 (6)
C10	0.0312 (8)	0.0642 (11)	0.0405 (8)	0.0012 (7)	0.0049 (6)	0.0004 (7)
C5	0.0403 (9)	0.0534 (10)	0.0358 (7)	0.0054 (7)	0.0095 (6)	0.0036 (7)
C25	0.0345 (8)	0.0643 (11)	0.0385 (8)	−0.0076 (8)	0.0069 (6)	0.0054 (7)
C1	0.0427 (10)	0.0620 (12)	0.0509 (9)	0.0114 (9)	0.0000 (8)	−0.0145 (9)
C24	0.0331 (8)	0.0616 (11)	0.0479 (9)	−0.0104 (8)	0.0022 (7)	−0.0002 (8)
C6	0.0394 (9)	0.0638 (11)	0.0500 (9)	0.0034 (8)	0.0121 (7)	−0.0015 (8)
C22	0.0511 (11)	0.0909 (15)	0.0356 (8)	−0.0186 (10)	0.0085 (7)	0.0009 (9)
C16	0.0585 (11)	0.0490 (9)	0.0337 (7)	0.0051 (8)	0.0131 (7)	0.0009 (7)
C2	0.0621 (12)	0.0564 (11)	0.0459 (9)	0.0184 (9)	−0.0036 (8)	−0.0010 (8)
C17	0.0856 (15)	0.0617 (12)	0.0319 (8)	0.0163 (11)	0.0102 (9)	0.0049 (8)
C3	0.0617 (12)	0.0435 (10)	0.0450 (9)	0.0041 (8)	0.0115 (8)	0.0025 (7)
C21	0.0464 (10)	0.0823 (14)	0.0395 (8)	−0.0263 (9)	0.0070 (7)	0.0000 (9)
C19	0.0455 (10)	0.0719 (13)	0.0424 (9)	0.0046 (9)	−0.0070 (7)	−0.0127 (9)
C18	0.0732 (14)	0.0810 (15)	0.0340 (8)	0.0263 (12)	−0.0098 (9)	−0.0059 (9)
C11	0.0514 (11)	0.0609 (12)	0.0614 (11)	0.0097 (9)	0.0019 (9)	−0.0120 (9)

Geometric parameters (Å, º) top

Cl1—C23	1.7433 (16)	C14—C19	1.381 (2)
Cl2—C1	1.7306 (19)	C10—H10A	0.9700
C9—C20	1.515 (2)	C10—H10B	0.9700
C9—C10	1.521 (2)	C5—C6	1.385 (2)
C9—C8	1.531 (2)	C5—H5	0.9300
C9—H9	1.007 (16)	C25—C24	1.383 (2)
N2—C13	1.351 (2)	C25—H25	0.9300
N2—C14	1.405 (2)	C1—C6	1.371 (3)
N2—H2A	0.85 (2)	C1—C2	1.376 (3)
C15—C16	1.377 (2)	C24—H24	0.9300
C15—C14	1.384 (2)	C6—H6	0.9300
C15—C12	1.5093 (19)	C22—C21	1.386 (2)
C7—O1	1.2096 (19)	C22—H22	0.9300
C7—C4	1.493 (2)	C16—C17	1.389 (3)
C7—C8	1.517 (2)	C16—H16	0.9300
O2—C13	1.2213 (19)	C2—C3	1.378 (3)
N1—C11	1.457 (2)	C2—H2	0.9300
N1—C10	1.458 (2)	C17—C18	1.381 (3)
N1—C12	1.4612 (19)	C17—H17	0.9300
C8—C12	1.579 (2)	C3—H3	0.9300
C8—H8	0.964 (15)	C21—H21	0.9300
C12—C13	1.546 (2)	C19—C18	1.381 (3)
C20—C25	1.380 (2)	C19—H19	0.9300
C20—C21	1.389 (2)	C18—H18	0.9300
C23—C22	1.370 (2)	C11—H11A	0.9600
C23—C24	1.372 (2)	C11—H11B	0.9600
C4—C5	1.388 (2)	C11—H11C	0.9600
C4—C3	1.390 (2)

C20—C9—C10	114.07 (14)	N1—C10—H10B	111.3
C20—C9—C8	116.12 (12)	C9—C10—H10B	111.3
C10—C9—C8	102.19 (13)	H10A—C10—H10B	109.2
C20—C9—H9	107.3 (9)	C6—C5—C4	120.88 (15)
C10—C9—H9	108.0 (9)	C6—C5—H5	119.6
C8—C9—H9	108.8 (9)	C4—C5—H5	119.6
C13—N2—C14	111.50 (14)	C20—C25—C24	121.60 (15)
C13—N2—H2A	121.4 (13)	C20—C25—H25	119.2
C14—N2—H2A	125.7 (14)	C24—C25—H25	119.2
C16—C15—C14	120.67 (14)	C6—C1—C2	121.22 (17)
C16—C15—C12	130.26 (15)	C6—C1—Cl2	119.63 (16)
C14—C15—C12	109.01 (13)	C2—C1—Cl2	119.16 (15)
O1—C7—C4	120.57 (15)	C23—C24—C25	119.21 (15)
O1—C7—C8	120.56 (15)	C23—C24—H24	120.4
C4—C7—C8	118.76 (13)	C25—C24—H24	120.4
C11—N1—C10	116.21 (14)	C1—C6—C5	119.13 (17)
C11—N1—C12	115.43 (13)	C1—C6—H6	120.4
C10—N1—C12	108.29 (12)	C5—C6—H6	120.4
C7—C8—C9	115.29 (13)	C23—C22—C21	119.11 (16)
C7—C8—C12	112.65 (12)	C23—C22—H22	120.4
C9—C8—C12	104.67 (12)	C21—C22—H22	120.4
C7—C8—H8	107.7 (9)	C15—C16—C17	118.25 (18)
C9—C8—H8	108.6 (9)	C15—C16—H16	120.9
C12—C8—H8	107.7 (9)	C17—C16—H16	120.9
N1—C12—C15	112.69 (12)	C1—C2—C3	119.36 (17)
N1—C12—C13	115.44 (13)	C1—C2—H2	120.3
C15—C12—C13	101.46 (12)	C3—C2—H2	120.3
N1—C12—C8	103.88 (11)	C18—C17—C16	120.42 (18)
C15—C12—C8	116.32 (13)	C18—C17—H17	119.8
C13—C12—C8	107.41 (11)	C16—C17—H17	119.8
C25—C20—C21	117.66 (14)	C2—C3—C4	120.78 (17)
C25—C20—C9	119.82 (13)	C2—C3—H3	119.6
C21—C20—C9	122.51 (14)	C4—C3—H3	119.6
C22—C23—C24	120.99 (15)	C22—C21—C20	121.43 (16)
C22—C23—Cl1	120.19 (13)	C22—C21—H21	119.3
C24—C23—Cl1	118.82 (13)	C20—C21—H21	119.3
C5—C4—C3	118.53 (15)	C18—C19—C14	117.30 (18)
C5—C4—C7	123.30 (14)	C18—C19—H19	121.3
C3—C4—C7	118.11 (15)	C14—C19—H19	121.3
O2—C13—N2	126.58 (15)	C17—C18—C19	121.72 (17)
O2—C13—C12	125.09 (14)	C17—C18—H18	119.1
N2—C13—C12	108.29 (13)	C19—C18—H18	119.1
C19—C14—C15	121.57 (16)	N1—C11—H11A	109.5
C19—C14—N2	128.82 (16)	N1—C11—H11B	109.5
C15—C14—N2	109.59 (13)	H11A—C11—H11B	109.5
N1—C10—C9	102.32 (13)	N1—C11—H11C	109.5
N1—C10—H10A	111.3	H11A—C11—H11C	109.5
C9—C10—H10A	111.3	H11B—C11—H11C	109.5

O1—C7—C8—C9	−7.3 (2)	C15—C12—C13—N2	1.53 (16)
C4—C7—C8—C9	176.42 (12)	C8—C12—C13—N2	−121.00 (14)
O1—C7—C8—C12	112.75 (16)	C16—C15—C14—C19	3.0 (2)
C4—C7—C8—C12	−63.54 (16)	C12—C15—C14—C19	−174.50 (15)
C20—C9—C8—C7	−83.09 (17)	C16—C15—C14—N2	−178.46 (14)
C10—C9—C8—C7	152.12 (12)	C12—C15—C14—N2	4.06 (17)
C20—C9—C8—C12	152.59 (13)	C13—N2—C14—C19	175.32 (17)
C10—C9—C8—C12	27.79 (14)	C13—N2—C14—C15	−3.10 (19)
C11—N1—C12—C15	77.91 (17)	C11—N1—C10—C9	173.24 (14)
C10—N1—C12—C15	−149.85 (13)	C12—N1—C10—C9	41.42 (15)
C11—N1—C12—C13	−38.02 (18)	C20—C9—C10—N1	−167.97 (12)
C10—N1—C12—C13	94.22 (15)	C8—C9—C10—N1	−41.82 (14)
C11—N1—C12—C8	−155.33 (13)	C3—C4—C5—C6	−2.5 (2)
C10—N1—C12—C8	−23.09 (15)	C7—C4—C5—C6	174.50 (15)
C16—C15—C12—N1	55.4 (2)	C21—C20—C25—C24	−0.2 (3)
C14—C15—C12—N1	−127.39 (14)	C9—C20—C25—C24	178.42 (16)
C16—C15—C12—C13	179.49 (16)	C22—C23—C24—C25	−0.1 (3)
C14—C15—C12—C13	−3.36 (16)	Cl1—C23—C24—C25	179.77 (14)
C16—C15—C12—C8	−64.4 (2)	C20—C25—C24—C23	0.5 (3)
C14—C15—C12—C8	112.81 (14)	C2—C1—C6—C5	2.7 (3)
C7—C8—C12—N1	−130.00 (12)	Cl2—C1—C6—C5	−177.68 (13)
C9—C8—C12—N1	−4.01 (14)	C4—C5—C6—C1	0.1 (3)
C7—C8—C12—C15	−5.56 (17)	C24—C23—C22—C21	−0.5 (3)
C9—C8—C12—C15	120.43 (14)	Cl1—C23—C22—C21	179.58 (17)
C7—C8—C12—C13	107.23 (14)	C14—C15—C16—C17	−2.3 (2)
C9—C8—C12—C13	−126.78 (12)	C12—C15—C16—C17	174.61 (16)
C10—C9—C20—C25	−102.97 (18)	C6—C1—C2—C3	−2.9 (3)
C8—C9—C20—C25	138.57 (16)	Cl2—C1—C2—C3	177.48 (14)
C10—C9—C20—C21	75.5 (2)	C15—C16—C17—C18	0.2 (3)
C8—C9—C20—C21	−42.9 (2)	C1—C2—C3—C4	0.3 (3)
O1—C7—C4—C5	157.76 (16)	C5—C4—C3—C2	2.3 (2)
C8—C7—C4—C5	−25.9 (2)	C7—C4—C3—C2	−174.86 (15)
O1—C7—C4—C3	−25.2 (2)	C23—C22—C21—C20	0.9 (3)
C8—C7—C4—C3	151.11 (14)	C25—C20—C21—C22	−0.5 (3)
C14—N2—C13—O2	−177.25 (17)	C9—C20—C21—C22	−179.06 (19)
C14—N2—C13—C12	0.80 (18)	C15—C14—C19—C18	−1.5 (3)
N1—C12—C13—O2	−58.2 (2)	N2—C14—C19—C18	−179.75 (17)
C15—C12—C13—O2	179.62 (16)	C16—C17—C18—C19	1.3 (3)
C8—C12—C13—O2	57.1 (2)	C14—C19—C18—C17	−0.6 (3)
N1—C12—C13—N2	123.69 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.85 (2)	2.06 (2)	2.876 (2)	160
C24—H24···O1ⁱⁱ	0.93	2.42	3.104 (2)	130

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₀Cl₂N₂O₂
M_r	451.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.4139 (2), 11.6957 (2), 16.5262 (2)
β (°)	102.037 (1)
V (Å³)	2157.64 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20528, 5426, 3812
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.03
No. of reflections	5426
No. of parameters	293
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.44

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
N2—H2A···O2ⁱ	0.85 (2)	2.06 (2)	2.876 (2)	160
C24—H24···O1ⁱⁱ	0.93	2.42	3.104 (2)	130

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

Acknowledgements

TS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS also thanks the DST for an Inspire fellowship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Coldham, I. & Hufton, R. (2005). Chem. Rev. 105, 2765–2810. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef 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

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Volume 67| Part 11| November 2011| Page o3128

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

3′-(4-Chloro­benzo­yl)-4′-(4-chloro­phen­yl)-1′-methyl­spiro­[indoline-3,2′-pyrrolidin]-2-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3′-(4-Chlorobenzoyl)-4′-(4-chlorophenyl)-1′-methylspiro[indoline-3,2′-pyrrolidin]-2-one