2-(Pyrrolidin-1-ylmeth­yl)isoindoline-1,3-dione

Sakthivel, P.; Joseph, P.S.; Sebastiyan, A.; Suvaikin, M.Y.; Ramesh, M.

doi:10.1107/S1600536807050519

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2-(Pyrrolidin-1-ylmethyl)isoindoline-1,3-dione

P. Sakthivel, P. S. Joseph, A. Sebastiyan, M. Y. Suvaikin and M. Ramesh

In the title compound, C₁₃H₁₄N₂O₂, the pyrrolidine ring adopts an envelope conformation. The crystal structure is stabilized by C—H

O and C—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050519/bt2534sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050519/bt2534Isup2.hkl Contains datablock I

CCDC reference: 667409

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (Wave) = 0.000 Å
R factor = 0.044
wR factor = 0.133
Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           34.22
           From the CIF: _reflns_number_total               2752
           Count of symmetry unique reflns         2789
           Completeness (_total/calc)             98.67%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Substitituted pyrrolidine compounds have been found to have antimicrobial antifungal activity against various pathogens except Basillus substilis (Amal Raj et al., 2003). Pyrrolidine derivatives possess anti-influenza virus (Stylianakis et al., 2003), anticonvulsant (Obniska & Zagorska, 2003; Obniska et al., 2005), and other antiviral (Kolocouris et al., 1994) activities. Phthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities (Lima et al., 2002; Orzeszka et al., 2000; Bailleux et al., 1993). Phthalimides have also served as starting materials and intermediates for synthesis of alkaloids (Couture et al., 1998) pharmacophores (Couture et al., 1997). Several optically active pyrrolidine compounds have been used as intermediates in controlled asymmetric synthesis (Suzuki et al., 1994). In view of its importance and to obtain more detailed information of the structure and conformation of the title compound, its crystal structure was determined.

All C—C and C—N bond lengths in the pyrrolidine ring are comparable with values in related pyrrolidine derivatives (Abdul Ajees et al., 2002).

The sum of the angles at N2 of the pyrrolidine ring (340.69°) is in accordance with sp³ hybridization. The pyrrolidine ring adopts an envelope conformation and puckering parameters q₂=0.3772 (2) Å and φ₂ = 359.7 (4)° (Cremer & Pople,1975). Atom N2 deviates by 0.248 (2) Å from the least squares plane through the remaining four C atoms (C10/C11/C12/C13) of the ring.

The pyrrolidine ring makes a dihedral angle of 78.72 (8)° with the isoindole-1–3-dione ring. The molecular structure is stabilized by C—H···O and C—H···N interactions (Table 2 and Fig 2.).

Related literature top

For related literature, see: Abdul Ajees et al. (2002); Amal Raj et al. (2003); Bailleux et al. (1993); Couture et al. (1997, 1998); Cremer & Pople (1975); Kolocouris et al. (1994); Lima et al. (2002); Obniska & Zagorska (2003); Obniska et al. (2005); Orzeszka et al. (2000); Stylianakis et al. (2003); Suzuki et al. (1994).

Experimental top

The title compound is synthesized by the Manich condensation of phthalimide (14.71 g, 0.1 mol), 37% aqueous formaldehyde (7.5 ml, 0.1 mol) and pyrrolidone (8.2 ml, 0.1 mol) at 5°C. It was recrystalized from ethanol. The sample melts at 106–107°C.

Structure description top

All C—C and C—N bond lengths in the pyrrolidine ring are comparable with values in related pyrrolidine derivatives (Abdul Ajees et al., 2002).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. : The structure of the title compound showing the atom numbering scheme with 50% probability dispalcement ellipsoids.
	Fig. 2. : View of intermolecular C—H.·O and C—H.·N interactions in the title compound.

2-(Pyrrolidin-1-ylmethyl)isoindoline-1,3-dione top

Crystal data top

C₁₃H₁₄N₂O₂	Least Squares Treatment of 25 SET4 setting angles.
M_r = 230.26	D_x = 1.287 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3270 reflections
a = 9.0609 (3) Å	θ = 2.3–26.9°
b = 10.0777 (3) Å	µ = 0.09 mm⁻¹
c = 13.0192 (3) Å	T = 293 K
V = 1188.82 (6) Å³	Prism, colorless
Z = 4	0.30 × 0.22 × 0.20 mm
F(000) = 488

Data collection top

Bruker Kappa-APEX2 diffractometer	2752 independent reflections
Radiation source: fine focus sealed tube	1943 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and φ scans	θ_max = 34.2°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→14
T_min = 0.974, T_max = 0.983	k = −13→15
10764 measured reflections	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0753P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.134	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.20 e Å⁻³
2752 reflections	Δρ_min = −0.21 e Å⁻³
155 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.017 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1957 Friedel pairs
Secondary atom site location: difference Fourier map

Crystal data top

C₁₃H₁₄N₂O₂	V = 1188.82 (6) Å³
M_r = 230.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.0609 (3) Å	µ = 0.09 mm⁻¹
b = 10.0777 (3) Å	T = 293 K
c = 13.0192 (3) Å	0.30 × 0.22 × 0.20 mm

Data collection top

Bruker Kappa-APEX2 diffractometer	2752 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1943 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.983	R_int = 0.023
10764 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
2752 reflections	Δρ_min = −0.21 e Å⁻³
155 parameters	Absolute structure: Flack (1983), 1957 Friedel pairs

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 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
O1	0.18398 (17)	0.21647 (14)	−0.06749 (9)	0.0629 (4)
O2	0.43688 (14)	0.14885 (13)	0.23098 (8)	0.0539 (4)
N1	0.30783 (15)	0.21825 (12)	0.08729 (9)	0.0410 (3)
N2	0.22703 (15)	0.43629 (14)	0.15153 (11)	0.0458 (4)
C1	0.23597 (17)	0.15773 (17)	0.00464 (10)	0.0427 (4)
C2	0.24128 (18)	0.01370 (17)	0.02426 (10)	0.0420 (4)
C3	0.1829 (2)	−0.0904 (2)	−0.03067 (13)	0.0574 (6)
C4	0.2072 (3)	−0.2164 (2)	0.00767 (17)	0.0692 (7)
C5	0.2855 (3)	−0.2374 (2)	0.09740 (18)	0.0687 (7)
C6	0.3435 (2)	−0.13266 (18)	0.15237 (15)	0.0536 (5)
C7	0.32003 (17)	−0.00686 (15)	0.11436 (10)	0.0403 (4)
C8	0.36506 (15)	0.12407 (15)	0.15516 (11)	0.0396 (4)
C9	0.33321 (18)	0.36197 (15)	0.09495 (12)	0.0444 (4)
C10	0.2215 (2)	0.4163 (2)	0.26207 (13)	0.0620 (6)
C11	0.0869 (3)	0.4946 (4)	0.29372 (18)	0.0900 (10)
C12	−0.0082 (3)	0.5043 (4)	0.19898 (18)	0.0905 (10)
C13	0.0746 (2)	0.4311 (2)	0.11634 (15)	0.0612 (6)
H3A	0.12962	−0.07660	−0.09079	0.0689*
H4A	0.16982	−0.28910	−0.02784	0.0830*
H5A	0.29935	−0.32358	0.12106	0.0824*
H6A	0.39631	−0.14643	0.21269	0.0642*
H9A	0.42910	0.37592	0.12627	0.0533*
H9B	0.33773	0.39790	0.02590	0.0533*
H10A	0.30976	0.45017	0.29506	0.0744*
H10B	0.21039	0.32302	0.27884	0.0744*
H11A	0.03441	0.44943	0.34846	0.1079*
H11B	0.11495	0.58223	0.31751	0.1079*
H12A	−0.10374	0.46376	0.21084	0.1084*
H12B	−0.02286	0.59635	0.17971	0.1084*
H13A	0.04060	0.34015	0.11058	0.0734*
H13B	0.06364	0.47467	0.05035	0.0734*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0758 (9)	0.0638 (8)	0.0492 (6)	0.0015 (8)	−0.0174 (6)	0.0122 (5)
O2	0.0591 (7)	0.0564 (7)	0.0462 (5)	−0.0071 (6)	−0.0155 (5)	0.0043 (5)
N1	0.0463 (7)	0.0364 (6)	0.0402 (5)	−0.0019 (5)	−0.0041 (5)	0.0042 (4)
N2	0.0445 (6)	0.0416 (7)	0.0514 (6)	−0.0014 (6)	−0.0012 (6)	0.0003 (5)
C1	0.0437 (7)	0.0471 (8)	0.0373 (6)	−0.0010 (6)	−0.0024 (6)	0.0030 (5)
C2	0.0434 (7)	0.0445 (8)	0.0382 (6)	−0.0015 (6)	0.0016 (5)	−0.0022 (5)
C3	0.0637 (11)	0.0584 (10)	0.0502 (8)	−0.0085 (9)	−0.0011 (8)	−0.0144 (7)
C4	0.0835 (14)	0.0493 (11)	0.0747 (12)	−0.0092 (11)	0.0059 (11)	−0.0199 (9)
C5	0.0834 (14)	0.0378 (9)	0.0848 (13)	0.0019 (10)	0.0067 (12)	0.0005 (9)
C6	0.0600 (10)	0.0418 (8)	0.0589 (9)	0.0041 (8)	−0.0001 (8)	0.0068 (7)
C7	0.0419 (7)	0.0384 (7)	0.0407 (6)	−0.0001 (6)	0.0010 (5)	0.0027 (5)
C8	0.0380 (6)	0.0424 (7)	0.0383 (6)	−0.0014 (6)	−0.0005 (5)	0.0054 (5)
C9	0.0432 (7)	0.0384 (7)	0.0516 (7)	−0.0055 (6)	0.0033 (6)	0.0075 (6)
C10	0.0626 (11)	0.0704 (12)	0.0531 (9)	0.0027 (10)	−0.0013 (8)	−0.0048 (8)
C11	0.0835 (16)	0.115 (2)	0.0715 (13)	0.0182 (17)	0.0118 (12)	−0.0226 (14)
C12	0.0615 (13)	0.120 (2)	0.0900 (16)	0.0255 (16)	0.0038 (12)	−0.0157 (17)
C13	0.0477 (9)	0.0724 (12)	0.0634 (10)	0.0053 (9)	−0.0076 (8)	−0.0028 (9)

Geometric parameters (Å, º) top

O1—C1	1.2059 (19)	C11—C12	1.508 (4)
O2—C8	1.2084 (18)	C12—C13	1.505 (4)
N1—C1	1.3978 (19)	C3—H3A	0.9300
N1—C8	1.3966 (19)	C4—H4A	0.9300
N1—C9	1.4699 (19)	C5—H5A	0.9300
N2—C9	1.425 (2)	C6—H6A	0.9300
N2—C10	1.454 (2)	C9—H9A	0.9700
N2—C13	1.456 (2)	C9—H9B	0.9700
C1—C2	1.475 (2)	C10—H10A	0.9700
C2—C3	1.375 (2)	C10—H10B	0.9700
C2—C7	1.389 (2)	C11—H11A	0.9700
C3—C4	1.382 (3)	C11—H11B	0.9700
C4—C5	1.383 (3)	C12—H12A	0.9700
C5—C6	1.379 (3)	C12—H12B	0.9700
C6—C7	1.377 (2)	C13—H13A	0.9700
C7—C8	1.480 (2)	C13—H13B	0.9700
C10—C11	1.510 (4)

O1···C13	3.375 (2)	C13···C2ⁱ	3.575 (2)
O1···C9ⁱ	3.295 (2)	C13···C1	3.441 (3)
O2···C10	3.352 (2)	C1···H13A	2.9000
O2···C6ⁱⁱ	3.334 (2)	C2···H11A^ix	3.0700
O2···C3ⁱⁱⁱ	3.340 (2)	C2···H13B^v	3.0800
O1···H9Aⁱ	2.6100	C6···H12A^ix	2.9700
O1···H9B	2.6000	C7···H13B^v	3.0900
O2···H9A	2.6600	C7···H12A^ix	3.0200
O2···H3Aⁱⁱⁱ	2.5100	C8···H10B	2.9300
O2···H10B	2.7700	H3A···O2^vi	2.5100
O2···H6Aⁱⁱ	2.6600	H5A···N2^vii	2.5400
N2···C5^iv	3.405 (2)	H6A···O2^viii	2.6600
N1···H10B	2.8500	H9A···O2	2.6600
N1···H13A	2.7300	H9A···H10A	2.5600
N2···H5A^iv	2.5400	H9A···O1^v	2.6100
C1···C13	3.441 (3)	H9B···O1	2.6000
C1···C13^v	3.563 (2)	H10A···H9A	2.5600
C2···C13^v	3.575 (2)	H10B···O2	2.7700
C3···O2^vi	3.340 (2)	H10B···N1	2.8500
C5···N2^vii	3.405 (2)	H10B···C8	2.9300
C6···O2^viii	3.334 (2)	H11A···C2^x	3.0700
C8···C10	3.508 (2)	H12A···C6^x	2.9700
C9···O1^v	3.295 (2)	H12A···C7^x	3.0200
C10···O2	3.352 (2)	H13A···N1	2.7300
C10···C8	3.508 (2)	H13A···C1	2.9000
C13···C1ⁱ	3.563 (2)	H13B···C2ⁱ	3.0800
C13···O1	3.375 (2)	H13B···C7ⁱ	3.0900

C1—N1—C8	111.31 (12)	C5—C4—H4A	119.00
C1—N1—C9	123.71 (12)	C4—C5—H5A	119.00
C8—N1—C9	124.65 (12)	C6—C5—H5A	119.00
C9—N2—C10	117.53 (14)	C5—C6—H6A	121.00
C9—N2—C13	117.33 (14)	C7—C6—H6A	121.00
C10—N2—C13	105.89 (14)	N1—C9—H9A	108.00
O1—C1—N1	124.56 (16)	N1—C9—H9B	108.00
O1—C1—C2	129.11 (15)	N2—C9—H9A	108.00
N1—C1—C2	106.32 (12)	N2—C9—H9B	108.00
C1—C2—C3	130.40 (14)	H9A—C9—H9B	107.00
C1—C2—C7	108.06 (13)	N2—C10—H10A	111.00
C3—C2—C7	121.54 (16)	N2—C10—H10B	111.00
C2—C3—C4	116.85 (17)	C11—C10—H10A	111.00
C3—C4—C5	121.83 (19)	C11—C10—H10B	111.00
C4—C5—C6	121.11 (19)	H10A—C10—H10B	109.00
C5—C6—C7	117.33 (18)	C10—C11—H11A	111.00
C2—C7—C6	121.34 (15)	C10—C11—H11B	111.00
C2—C7—C8	108.17 (13)	C12—C11—H11A	111.00
C6—C7—C8	130.48 (14)	C12—C11—H11B	111.00
O2—C8—N1	125.19 (14)	H11A—C11—H11B	109.00
O2—C8—C7	128.76 (14)	C11—C12—H12A	111.00
N1—C8—C7	106.05 (12)	C11—C12—H12B	111.00
N1—C9—N2	116.58 (13)	C13—C12—H12A	111.00
N2—C10—C11	103.03 (16)	C13—C12—H12B	111.00
C10—C11—C12	105.8 (2)	H12A—C12—H12B	109.00
C11—C12—C13	105.6 (2)	N2—C13—H13A	111.00
N2—C13—C12	103.32 (17)	N2—C13—H13B	111.00
C2—C3—H3A	122.00	C12—C13—H13A	111.00
C4—C3—H3A	122.00	C12—C13—H13B	111.00
C3—C4—H4A	119.00	H13A—C13—H13B	109.00

C8—N1—C1—O1	−175.81 (15)	N1—C1—C2—C3	177.47 (17)
C9—N1—C1—O1	−2.0 (2)	C3—C2—C7—C6	0.3 (2)
C8—N1—C1—C2	3.08 (16)	C1—C2—C7—C6	−179.93 (14)
C9—N1—C1—C2	176.87 (13)	C1—C2—C7—C8	0.79 (17)
C9—N1—C8—C7	−176.32 (13)	C1—C2—C3—C4	179.79 (18)
C1—N1—C9—N2	94.98 (17)	C7—C2—C3—C4	−0.4 (3)
C8—N1—C9—N2	−92.06 (18)	C3—C2—C7—C8	−179.03 (15)
C1—N1—C8—C7	−2.60 (16)	C2—C3—C4—C5	0.5 (3)
C1—N1—C8—O2	177.17 (14)	C3—C4—C5—C6	−0.3 (4)
C9—N1—C8—O2	3.5 (2)	C4—C5—C6—C7	0.1 (3)
C10—N2—C9—N1	69.20 (19)	C5—C6—C7—C2	−0.1 (3)
C13—N2—C10—C11	−39.5 (2)	C5—C6—C7—C8	179.03 (18)
C9—N2—C13—C12	173.19 (19)	C2—C7—C8—N1	1.04 (16)
C10—N2—C13—C12	39.7 (2)	C2—C7—C8—O2	−178.72 (15)
C13—N2—C9—N1	−58.89 (19)	C6—C7—C8—O2	2.1 (3)
C9—N2—C10—C11	−172.84 (18)	C6—C7—C8—N1	−178.15 (16)
O1—C1—C2—C3	−3.7 (3)	N2—C10—C11—C12	23.4 (3)
N1—C1—C2—C7	−2.33 (17)	C10—C11—C12—C13	0.2 (3)
O1—C1—C2—C7	176.49 (17)	C11—C12—C13—N2	−23.6 (3)

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1/2, −y, z+1/2; (iv) x, y+1, z; (v) x+1/2, −y+1/2, −z; (vi) −x+1/2, −y, z−1/2; (vii) x, y−1, z; (viii) −x+1, y−1/2, −z+1/2; (ix) −x, y−1/2, −z+1/2; (x) −x, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2^vi	0.9300	2.5100	3.340 (2)	149.00
C5—H5A···N2^vii	0.9300	2.5400	3.405 (2)	155.00

Symmetry codes: (vi) −x+1/2, −y, z−1/2; (vii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂O₂
M_r	230.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.0609 (3), 10.0777 (3), 13.0192 (3)
V (Å³)	1188.82 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa-APEX2
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	10764, 2752, 1943
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.791

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.134, 1.03
No. of reflections	2752
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21
Absolute structure	Flack (1983), 1957 Friedel pairs

Computer programs: APEX2 (Bruker, 2004), APEX2/SAINT (Bruker, 2004), SAINT/XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-32 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.9300	2.5100	3.340 (2)	149.00
C5—H5A···N2ⁱⁱ	0.9300	2.5400	3.405 (2)	155.00

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

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