Methyl 4′-(4-fluoro­phen­yl)-1′-methyl-3′-nitro­methyl-2-oxospiro­[indoline-3,2′-pyrrolidine]-3′-carboxyl­ate

Revathi, B.K.; Sathya, S.; Usha, G.; Murugan, G.; Bakthadoss, M.

doi:10.1107/S1600536813001578

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o278

doi:10.1107/S1600536813001578

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Methyl 4′-(4-fluorophenyl)-1′-methyl-3′-nitromethyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate

B. K. Revathi,^a S. Sathya,^a G. Usha,^a ^* G. Murugan ^b and M. Bakthadoss ^b

^aPost Graduate and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai-25, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

(Received 2 January 2013; accepted 16 January 2013; online 23 January 2013)

In the title compound, C₂₁H₂₀FN₃O₅, the the pyrrolidine ring makes dihedral angles of 84.91 (6) and 62.38 (7)° with the oxindole unit and the fluorophenyl ring, respectively. The pyrrolidine ring assumes an envelope conformation with the spiro C atom as the flap. The crystal packing features weak N—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For background to pyrrolidine derivatives, see: Raj et al. (2003 ); Cordell (1981 ); Usha et al. (2005 ).

Experimental

Crystal data

C₂₁H₂₀FN₃O₅
M_r = 413.40
Orthorhombic, P n a 2₁
a = 8.0265 (5) Å
b = 25.7011 (15) Å
c = 9.7763 (6) Å
V = 2016.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.979, T_max = 0.981
22124 measured reflections
2551 independent reflections
2355 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.132
S = 1.13
2551 reflections
271 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.86	2.34	3.127 (2)	152
C4—H4⋯O1ⁱ	0.93	2.42	3.223 (2)	145
C9—H9B⋯O1ⁱⁱ	0.97	2.49	3.314 (2)	142
C9—H9A⋯O4ⁱⁱⁱ	0.97	2.51	3.443 (3)	160
Symmetry codes: (i) $[-x, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x, -y, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813001578/bh2472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001578/bh2472Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001578/bh2472Isup3.cml

checkCIF report

Comment top

Pyrrolidine ring system is a frequently encountered structural motif in many biologically relevant alkaloids (Cordell, 1981). Substituted pyrrolidines possess anti-microbial and anti-fungal activity against various pathogens (Raj et al., 2003). In the title compound (Fig. 1), the N—C and C—C bond lengths are slightly longer than the normal values, but are comparable with those in other reported structures (e.g. Usha et al., 2005). This may be due to the spiro-atom character and the steric forces of bulky substituents in the pyrrolidine moiety. Bond length C7—O1, 1.226 (3) Å, indicates a keto group character. The dihedral angle [84.91 (6)°] between oxindole moiety and pyrrolidine ring shows that they are almost orthogonal to each other. The sum of the angles around N2 atom, 360.0°, and N3 atom, 359.9°, is an indication of their sp² hybridization. The O atoms of the nitro group have somewhat higher displacement parameters than the other atoms, indicating greater thermal motion for these atoms. The pyrrolidine ring adopts envelope conformation, with C8 as the flap.

The crystal packing is stabilized by weak N—H···N and C—H···O hydrogen bonds. The symmetry-related molecules linked through alternate N—H···N and C—H···O type hydrogen bonds are forming loops. These units running along [001] form molecular chains, which are connected by C—H···O hydrogen bonds, resulting in molecular layers (Fig. 2).

Related literature top

For background to pyrrolidine derivatives, see: Raj et al. (2003); Cordell (1981); Usha et al. (2005).

Experimental top

A mixture of (E)-methyl 3-(4-fluorophenyl)-2-(nitromethyl)acrylate (1 mmol, 0.24 g), isatin (1 mmol, 0.15 g) and sarcosine (1 mmol, 0.09 g) in acetonitrile (6 ml) was refluxed for 14 h. After completion of the reaction, as indicated by TLC, the reaction mixture was concentrated, and the resulting crude diluted with water (10 ml), and extracted with ethyl acetate (3 × 10 ml). The combined organic layers were washed with brine (2 × 10 ml) and dried over anhydrous Na₂SO₄. The organic layer thus obtained was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (Acme 100–200 mesh), using ethyl acetate:hexanes (3:7), to afford the title compound as a colourless solid, in 68% yield.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); 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, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the molecules in the crystal structure. The dashed lines indicate the hydrogen bonds.

Methyl 4'-(4-fluorophenyl)-1'-methyl-3'-nitromethyl-2-oxospiro[indoline-3,2'-pyrrolidine]-3'-carboxylate top

Crystal data top

C₂₁H₂₀FN₃O₅	F(000) = 864
M_r = 413.40	D_x = 1.362 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	θ = 2.2–28.0°
a = 8.0265 (5) Å	µ = 0.10 mm⁻¹
b = 25.7011 (15) Å	T = 293 K
c = 9.7763 (6) Å	Block, colourless
V = 2016.8 (2) Å³	0.20 × 0.18 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2551 independent reflections
Radiation source: fine-focus sealed tube	2355 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω and ϕ scan	θ_max = 28.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
T_min = 0.979, T_max = 0.981	k = −33→33
22124 measured reflections	l = −12→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2551 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³
0 constraints

Crystal data top

C₂₁H₂₀FN₃O₅	V = 2016.8 (2) Å³
M_r = 413.40	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.0265 (5) Å	µ = 0.10 mm⁻¹
b = 25.7011 (15) Å	T = 293 K
c = 9.7763 (6) Å	0.20 × 0.18 × 0.18 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2551 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2355 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.981	R_int = 0.022
22124 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.132	H-atom parameters constrained
S = 1.13	Δρ_max = 0.30 e Å⁻³
2551 reflections	Δρ_min = −0.16 e Å⁻³
271 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.3956 (3)	0.11630 (9)	0.1303 (3)	0.0495 (5)
H1	0.4261	0.1306	0.2140	0.059*
C2	0.4898 (3)	0.12602 (10)	0.0138 (3)	0.0565 (6)
H2	0.5850	0.1465	0.0206	0.068*
C3	0.4449 (3)	0.10596 (11)	−0.1112 (3)	0.0587 (6)
H3	0.5085	0.1137	−0.1880	0.070*
C4	0.3039 (3)	0.07382 (10)	−0.1246 (3)	0.0547 (5)
H4	0.2729	0.0599	−0.2086	0.066*
C5	0.2141 (3)	0.06398 (8)	−0.0077 (3)	0.0451 (5)
C6	0.2544 (3)	0.08481 (7)	0.1197 (2)	0.0427 (4)
C7	0.0156 (3)	0.03050 (8)	0.1341 (3)	0.0493 (5)
C8	0.1232 (3)	0.06782 (7)	0.2227 (2)	0.0411 (4)
C9	0.2291 (3)	0.08136 (9)	0.4461 (3)	0.0514 (5)
H9A	0.3491	0.0856	0.4421	0.062*
H9B	0.1982	0.0717	0.5386	0.062*
C10	0.1406 (2)	0.13220 (7)	0.4033 (2)	0.0390 (4)
H10	0.2258	0.1548	0.3629	0.047*
C11	0.0209 (2)	0.11542 (7)	0.2839 (2)	0.0365 (4)
C12	0.0607 (3)	0.16266 (9)	0.5181 (2)	0.0456 (5)
C13	0.0601 (4)	0.21706 (11)	0.5106 (3)	0.0588 (6)
H13	0.1131	0.2333	0.4375	0.071*
C14	−0.0166 (5)	0.24707 (14)	0.6083 (4)	0.0829 (11)
H14	−0.0177	0.2832	0.6014	0.099*
C15	−0.0913 (5)	0.2224 (2)	0.7158 (4)	0.0902 (13)
C16	−0.0913 (5)	0.1694 (2)	0.7311 (3)	0.0904 (13)
H16	−0.1425	0.1539	0.8060	0.109*
C17	−0.0125 (4)	0.13928 (14)	0.6316 (3)	0.0628 (7)
H17	−0.0088	0.1033	0.6412	0.075*
C18	−0.1491 (3)	0.09642 (8)	0.3340 (2)	0.0466 (5)
H18A	−0.2032	0.0778	0.2601	0.056*
H18B	−0.1318	0.0720	0.4082	0.056*
C19	−0.0041 (3)	0.15462 (7)	0.1679 (2)	0.0390 (4)
C20	0.0779 (4)	0.23421 (12)	0.0716 (4)	0.0769 (10)
H20A	0.1486	0.2634	0.0914	0.115*
H20B	−0.0350	0.2459	0.0619	0.115*
H20C	0.1137	0.2180	−0.0119	0.115*
C21	0.2968 (4)	−0.00037 (11)	0.3289 (4)	0.0769 (9)
H21A	0.3231	−0.0156	0.4159	0.115*
H21B	0.3961	0.0138	0.2889	0.115*
H21C	0.2515	−0.0265	0.2694	0.115*
N1	0.1739 (3)	0.04125 (7)	0.3481 (2)	0.0503 (4)
N2	0.0717 (2)	0.03194 (7)	0.0047 (2)	0.0506 (5)
H2A	0.0266	0.0154	−0.0622	0.061*
N3	−0.2642 (2)	0.13883 (9)	0.3830 (2)	0.0558 (5)
O1	−0.0977 (3)	0.00319 (8)	0.1779 (2)	0.0701 (6)
O2	−0.0938 (2)	0.14544 (7)	0.0731 (2)	0.0534 (4)
O3	0.0879 (2)	0.19697 (6)	0.18238 (18)	0.0467 (4)
O4	−0.3674 (3)	0.12634 (12)	0.4665 (3)	0.0891 (8)
O5	−0.2541 (3)	0.18170 (9)	0.3327 (3)	0.0725 (6)
F	−0.1702 (4)	0.25155 (16)	0.8126 (3)	0.1407 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0430 (10)	0.0469 (11)	0.0586 (13)	−0.0016 (9)	−0.0007 (10)	−0.0078 (10)
C2	0.0408 (10)	0.0505 (12)	0.0781 (17)	−0.0041 (9)	0.0071 (11)	−0.0067 (12)
C3	0.0542 (12)	0.0576 (13)	0.0644 (15)	−0.0041 (10)	0.0159 (12)	−0.0052 (12)
C4	0.0578 (12)	0.0523 (12)	0.0539 (12)	−0.0018 (10)	0.0035 (11)	−0.0060 (10)
C5	0.0449 (10)	0.0352 (9)	0.0553 (12)	0.0008 (8)	0.0011 (9)	−0.0069 (9)
C6	0.0434 (10)	0.0346 (9)	0.0501 (11)	0.0033 (7)	−0.0005 (9)	0.0002 (8)
C7	0.0603 (12)	0.0302 (9)	0.0573 (13)	−0.0074 (8)	0.0015 (11)	−0.0072 (9)
C8	0.0477 (10)	0.0302 (8)	0.0455 (10)	−0.0024 (7)	−0.0014 (9)	−0.0011 (8)
C9	0.0537 (11)	0.0453 (11)	0.0551 (12)	−0.0007 (10)	−0.0151 (11)	0.0084 (10)
C10	0.0439 (9)	0.0360 (8)	0.0371 (9)	−0.0064 (7)	−0.0058 (8)	0.0027 (7)
C11	0.0409 (9)	0.0321 (8)	0.0364 (9)	−0.0035 (7)	−0.0031 (7)	−0.0007 (7)
C12	0.0476 (10)	0.0525 (12)	0.0369 (10)	−0.0055 (9)	−0.0060 (9)	−0.0045 (9)
C13	0.0703 (15)	0.0514 (13)	0.0546 (14)	−0.0030 (11)	−0.0120 (12)	−0.0122 (11)
C14	0.099 (2)	0.080 (2)	0.070 (2)	0.0254 (18)	−0.0267 (18)	−0.0332 (18)
C15	0.083 (2)	0.133 (4)	0.0544 (17)	0.037 (2)	−0.0180 (16)	−0.039 (2)
C16	0.0714 (19)	0.161 (4)	0.0392 (13)	0.000 (2)	0.0035 (13)	−0.0025 (19)
C17	0.0645 (15)	0.0838 (19)	0.0401 (12)	−0.0096 (13)	−0.0040 (11)	0.0066 (12)
C18	0.0481 (10)	0.0426 (10)	0.0491 (11)	−0.0088 (8)	0.0016 (10)	−0.0030 (9)
C19	0.0414 (9)	0.0357 (9)	0.0397 (10)	0.0009 (7)	−0.0033 (8)	0.0013 (8)
C20	0.089 (2)	0.0620 (16)	0.079 (2)	−0.0208 (14)	−0.0223 (17)	0.0373 (16)
C21	0.087 (2)	0.0523 (14)	0.091 (2)	0.0249 (14)	−0.002 (2)	0.0125 (14)
N1	0.0629 (11)	0.0336 (8)	0.0543 (10)	0.0054 (8)	−0.0047 (9)	0.0061 (8)
N2	0.0552 (10)	0.0433 (10)	0.0532 (11)	−0.0086 (7)	0.0016 (9)	−0.0114 (8)
N3	0.0382 (9)	0.0719 (13)	0.0573 (12)	−0.0055 (8)	−0.0024 (9)	−0.0161 (11)
O1	0.0878 (13)	0.0495 (10)	0.0729 (12)	−0.0332 (9)	0.0181 (11)	−0.0134 (9)
O2	0.0571 (9)	0.0571 (9)	0.0460 (9)	−0.0035 (7)	−0.0132 (8)	0.0043 (7)
O3	0.0568 (8)	0.0361 (7)	0.0472 (8)	−0.0059 (6)	−0.0068 (7)	0.0092 (6)
O4	0.0599 (11)	0.1159 (19)	0.0916 (18)	−0.0154 (12)	0.0277 (12)	−0.0243 (16)
O5	0.0721 (12)	0.0647 (11)	0.0806 (14)	0.0173 (9)	0.0032 (11)	−0.0056 (11)
F	0.131 (2)	0.222 (4)	0.0689 (15)	0.078 (2)	−0.0131 (14)	−0.0631 (18)

Geometric parameters (Å, º) top

C1—C2	1.389 (4)	C12—C13	1.400 (4)
C1—C6	1.396 (3)	C13—C14	1.374 (4)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.375 (4)	C14—C15	1.365 (7)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.407 (3)	C15—F	1.363 (4)
C3—H3	0.9300	C15—C16	1.372 (7)
C4—C5	1.374 (3)	C16—C17	1.394 (5)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.394 (3)	C17—H17	0.9300
C5—N2	1.414 (3)	C18—N3	1.507 (3)
C6—C8	1.521 (3)	C18—H18A	0.9700
C7—O1	1.226 (3)	C18—H18B	0.9700
C7—N2	1.343 (3)	C19—O2	1.196 (3)
C7—C8	1.554 (3)	C19—O3	1.323 (2)
C8—N1	1.460 (3)	C20—O3	1.447 (3)
C8—C11	1.590 (3)	C20—H20A	0.9600
C9—N1	1.476 (3)	C20—H20B	0.9600
C9—C10	1.545 (3)	C20—H20C	0.9600
C9—H9A	0.9700	C21—N1	1.467 (3)
C9—H9B	0.9700	C21—H21A	0.9600
C10—C12	1.511 (3)	C21—H21B	0.9600
C10—C11	1.573 (3)	C21—H21C	0.9600
C10—H10	0.9800	N2—H2A	0.8600
C11—C18	1.529 (3)	N3—O4	1.207 (3)
C11—C19	1.530 (3)	N3—O5	1.209 (3)
C12—C17	1.392 (4)

C2—C1—C6	119.0 (2)	C13—C12—C10	118.7 (2)
C2—C1—H1	120.5	C14—C13—C12	121.7 (3)
C6—C1—H1	120.5	C14—C13—H13	119.1
C3—C2—C1	121.2 (2)	C12—C13—H13	119.1
C3—C2—H2	119.4	C15—C14—C13	118.1 (3)
C1—C2—H2	119.4	C15—C14—H14	120.9
C2—C3—C4	120.9 (2)	C13—C14—H14	120.9
C2—C3—H3	119.5	F—C15—C14	119.0 (4)
C4—C3—H3	119.5	F—C15—C16	118.0 (4)
C5—C4—C3	116.9 (2)	C14—C15—C16	123.0 (3)
C5—C4—H4	121.6	C15—C16—C17	118.4 (4)
C3—C4—H4	121.6	C15—C16—H16	120.8
C4—C5—C6	123.4 (2)	C17—C16—H16	120.8
C4—C5—N2	127.0 (2)	C12—C17—C16	120.5 (4)
C6—C5—N2	109.5 (2)	C12—C17—H17	119.7
C5—C6—C1	118.5 (2)	C16—C17—H17	119.7
C5—C6—C8	108.73 (18)	N3—C18—C11	114.69 (17)
C1—C6—C8	132.8 (2)	N3—C18—H18A	108.6
O1—C7—N2	126.4 (2)	C11—C18—H18A	108.6
O1—C7—C8	124.8 (2)	N3—C18—H18B	108.6
N2—C7—C8	108.78 (19)	C11—C18—H18B	108.6
N1—C8—C6	119.80 (19)	H18A—C18—H18B	107.6
N1—C8—C7	109.50 (17)	O2—C19—O3	125.5 (2)
C6—C8—C7	101.10 (18)	O2—C19—C11	121.53 (18)
N1—C8—C11	100.84 (17)	O3—C19—C11	112.90 (17)
C6—C8—C11	112.69 (16)	O3—C20—H20A	109.5
C7—C8—C11	113.42 (18)	O3—C20—H20B	109.5
N1—C9—C10	106.07 (17)	H20A—C20—H20B	109.5
N1—C9—H9A	110.5	O3—C20—H20C	109.5
C10—C9—H9A	110.5	H20A—C20—H20C	109.5
N1—C9—H9B	110.5	H20B—C20—H20C	109.5
C10—C9—H9B	110.5	N1—C21—H21A	109.5
H9A—C9—H9B	108.7	N1—C21—H21B	109.5
C12—C10—C9	115.6 (2)	H21A—C21—H21B	109.5
C12—C10—C11	115.70 (16)	N1—C21—H21C	109.5
C9—C10—C11	104.48 (16)	H21A—C21—H21C	109.5
C12—C10—H10	106.8	H21B—C21—H21C	109.5
C9—C10—H10	106.8	C8—N1—C21	114.9 (2)
C11—C10—H10	106.8	C8—N1—C9	107.58 (16)
C18—C11—C19	109.31 (17)	C21—N1—C9	113.0 (2)
C18—C11—C10	113.27 (17)	C7—N2—C5	111.58 (19)
C19—C11—C10	116.74 (15)	C7—N2—H2A	124.2
C18—C11—C8	109.60 (16)	C5—N2—H2A	124.2
C19—C11—C8	107.18 (16)	O4—N3—O5	124.3 (3)
C10—C11—C8	100.04 (15)	O4—N3—C18	116.3 (2)
C17—C12—C13	118.1 (3)	O5—N3—C18	119.3 (2)
C17—C12—C10	123.2 (2)	C19—O3—C20	115.7 (2)

C6—C1—C2—C3	1.1 (4)	C9—C10—C12—C17	−34.3 (3)
C1—C2—C3—C4	−1.6 (4)	C11—C10—C12—C17	88.4 (3)
C2—C3—C4—C5	0.4 (4)	C9—C10—C12—C13	145.6 (2)
C3—C4—C5—C6	1.2 (4)	C11—C10—C12—C13	−91.8 (2)
C3—C4—C5—N2	−178.1 (2)	C17—C12—C13—C14	−3.0 (4)
C4—C5—C6—C1	−1.7 (3)	C10—C12—C13—C14	177.2 (2)
N2—C5—C6—C1	177.79 (19)	C12—C13—C14—C15	1.0 (5)
C4—C5—C6—C8	177.1 (2)	C13—C14—C15—F	−179.0 (3)
N2—C5—C6—C8	−3.4 (2)	C13—C14—C15—C16	0.8 (5)
C2—C1—C6—C5	0.5 (3)	F—C15—C16—C17	179.3 (3)
C2—C1—C6—C8	−177.9 (2)	C14—C15—C16—C17	−0.6 (5)
C5—C6—C8—N1	125.3 (2)	C13—C12—C17—C16	3.2 (4)
C1—C6—C8—N1	−56.2 (3)	C10—C12—C17—C16	−177.0 (3)
C5—C6—C8—C7	5.0 (2)	C15—C16—C17—C12	−1.5 (5)
C1—C6—C8—C7	−176.4 (2)	C19—C11—C18—N3	−57.6 (2)
C5—C6—C8—C11	−116.37 (19)	C10—C11—C18—N3	74.4 (2)
C1—C6—C8—C11	62.2 (3)	C8—C11—C18—N3	−174.82 (19)
O1—C7—C8—N1	45.3 (3)	C18—C11—C19—O2	−49.3 (3)
N2—C7—C8—N1	−132.4 (2)	C10—C11—C19—O2	−179.5 (2)
O1—C7—C8—C6	172.7 (2)	C8—C11—C19—O2	69.4 (3)
N2—C7—C8—C6	−5.1 (2)	C18—C11—C19—O3	133.43 (19)
O1—C7—C8—C11	−66.4 (3)	C10—C11—C19—O3	3.2 (2)
N2—C7—C8—C11	115.8 (2)	C8—C11—C19—O3	−107.87 (19)
N1—C9—C10—C12	133.5 (2)	C6—C8—N1—C21	−45.7 (3)
N1—C9—C10—C11	5.2 (2)	C7—C8—N1—C21	70.3 (3)
C12—C10—C11—C18	−41.3 (2)	C11—C8—N1—C21	−169.9 (2)
C9—C10—C11—C18	87.1 (2)	C6—C8—N1—C9	81.1 (2)
C12—C10—C11—C19	87.0 (2)	C7—C8—N1—C9	−162.96 (19)
C9—C10—C11—C19	−144.63 (19)	C11—C8—N1—C9	−43.2 (2)
C12—C10—C11—C8	−157.81 (18)	C10—C9—N1—C8	24.4 (2)
C9—C10—C11—C8	−29.5 (2)	C10—C9—N1—C21	152.3 (2)
N1—C8—C11—C18	−75.4 (2)	O1—C7—N2—C5	−174.3 (3)
C6—C8—C11—C18	155.62 (19)	C8—C7—N2—C5	3.4 (3)
C7—C8—C11—C18	41.5 (2)	C4—C5—N2—C7	179.4 (2)
N1—C8—C11—C19	166.04 (16)	C6—C5—N2—C7	0.0 (3)
C6—C8—C11—C19	37.1 (2)	C11—C18—N3—O4	−153.5 (2)
C7—C8—C11—C19	−77.0 (2)	C11—C18—N3—O5	30.2 (3)
N1—C8—C11—C10	43.83 (18)	O2—C19—O3—C20	−0.8 (4)
C6—C8—C11—C10	−85.1 (2)	C11—C19—O3—C20	176.3 (2)
C7—C8—C11—C10	160.79 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.34	3.127 (2)	152
C4—H4···O1ⁱ	0.93	2.42	3.223 (2)	145
C9—H9B···O1ⁱⁱ	0.97	2.49	3.314 (2)	142
C9—H9A···O4ⁱⁱⁱ	0.97	2.51	3.443 (3)	160

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀FN₃O₅
M_r	413.40
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	8.0265 (5), 25.7011 (15), 9.7763 (6)
V (Å³)	2016.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.979, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	22124, 2551, 2355
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.132, 1.13
No. of reflections	2551
No. of parameters	271
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), 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···N1ⁱ	0.86	2.34	3.127 (2)	151.8
C4—H4···O1ⁱ	0.93	2.42	3.223 (2)	145.0
C9—H9B···O1ⁱⁱ	0.97	2.49	3.314 (2)	142.1
C9—H9A···O4ⁱⁱⁱ	0.97	2.51	3.443 (3)	160.2

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

Acknowledgements

The authors thank Professor D. Velmurugan (Centre for Advanced Study in Crystallography and Biophysics, University of Madras) for providing data collection and computer facilities.

References

Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cordell, G. A. (1981). In Introduction to Alkaloids: A Biogenetic Approach. New York: Wiley International. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Raj, A. A., Raghunathan, R., SrideviKumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–419. Web of Science CrossRef PubMed CAS 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
Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jaisankar, P. & Srinivasan, P. C. (2005). Acta Cryst. E61, o2227–o2229. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 69| Part 2| February 2013| Page o278

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

Methyl 4′-(4-fluoro­phen­yl)-1′-methyl-3′-nitro­methyl-2-oxo­spiro­[indoline-3,2′-pyrrolidine]-3′-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

Methyl 4′-(4-fluorophenyl)-1′-methyl-3′-nitromethyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate