Crystal structure of N-(3-hy­droxy­phenyl)succinimide

Suchetan, P.A.; Naveen, S.; Lokanath, N.K.; Sreenivasa, S.

doi:10.1107/S1600536814016328

organic compounds

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Volume 70| Part 9| September 2014| Page o927

doi:10.1107/S1600536814016328

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Crystal structure of N-(3-hydroxyphenyl)succinimide

P. A. Suchetan,^a S. Naveen,^b N. K. Lokanath ^c and S. Sreenivasa ^d ^*

^aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^bInstitution of Excellence, Vijnana Bhavan, University of Mysore, Manasagangotri, Mysore 570023, India, ^cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and ^dDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: drsreenivasa@yahoo.co.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 July 2014; accepted 14 July 2014; online 1 August 2014)

In the title compound, C₁₀H₉NO₃, the dihedral angle between the benzene and pyrrolidine rings is 53.9 (1)°. In the crystal, molecules are linked through strong O—H⋯O hydrogen bonds into zigzag C(8) chains running along [010]. The chains are linked by C—H⋯π interactions forming sheets lying parallel to (100).

Keywords: crystal structure; succinimide; hydrogen bonding.

CCDC reference: 1013858

1. Related literature

For the crystal structures of the 3-methyl and 3-chloro derivatives of N-phenylsuccinimide, see: Saraswathi et al. (2010 , 2011 ).

2. Experimental

2.1. Crystal data

C₁₀H₉NO₃
M_r = 191.18
Monoclinic, P 2₁ /c
a = 11.432 (2) Å
b = 7.6567 (14) Å
c = 10.115 (2) Å
β = 98.688 (7)°
V = 875.2 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.91 mm⁻¹
T = 293 K
0.42 × 0.31 × 0.19 mm

2.2. Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.749, T_max = 0.841
3786 measured reflections
1234 independent reflections
1207 reflections with I > 2σ(I)
R_int = 0.028
θ_max = 60.0°

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.140
S = 1.20
1234 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.94 (4)	1.82 (4)	2.758 (2)	175 (4)
C8—H8A⋯Cgⁱⁱ	0.97	2.83	3.613 (3)	138
C9—H9A⋯Cgⁱⁱ	0.97	2.79	3.579 (3)	139
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1013858

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814016328/su2752sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016328/su2752Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016328/su2752Isup3.cml

checkCIF report

Introduction top

As a part of a study on the effect of ring and side-chain substitutions on N-(Aryl)-succinimides (Saraswathi et al., 2010,2011), the title compound has been synthesized and we report herein on its crystal structure.

Experimental top

Synthesis and crystallization top

The title compound was prepared according to the reported procedure (Saraswathi et al., 2010,2011). Colourless prisms of the title compound were obtained by slow evaporation of an aqueous methanolic solution at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydroxyl H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were positioned with idealized geometry and treated as riding atoms: C—H = 0.93-0.97 Å with U_iso(H) = 1.2U_eq(C).

Results and discussion top

The title molecule, Fig. 1, is non-planar with the benzene and pyrrolidine [r.m.s. deviation = 0.039 Å] rings tilted at 53.9 (1) °. This is close to the values of 52.5 (1) and 59.5 (1) ° observed in N-(3-methylphenyl)-succinimide (Saraswathi et al. 2010) and N-(3-chlorophenyl)-succinimide (Saraswathi et al. 2011).

In the crystal, molecules are linked through strong O—H···O hydrogen bonds into zigzag C(8) chains running along [010] (Table 1 and Fig. 2). The chains are linked by C—H···π interactions (Table 1 Fig. 3) forming sheets lying parallel to (100).

Related literature top

For the crystal structures of the 3-methyl and 3-chloro derivatives of N-phenylsuccinimide, see: Saraswathi et al. (2010, 2011).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title molecule, with atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound, showing the formation of the zigzag C(8) chains through O—H···O hydrogen bonds (dashed lines; see Table 1 for details).
	Fig. 3. A partial view along the a axis of the crystal packing of the title compound, showing the C—H···π interactions (dashed lines; see Table 1 for details).

1-(3-Hydroxyphenyl)pyrrolidine-2,5-dione top

Crystal data top

C₁₀H₉NO₃	Prism
M_r = 191.18	D_x = 1.451 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 393 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 11.432 (2) Å	Cell parameters from 25 reflections
b = 7.6567 (14) Å	θ = 3.9–60.0°
c = 10.115 (2) Å	µ = 0.91 mm⁻¹
β = 98.688 (7)°	T = 293 K
V = 875.2 (3) Å³	Prism, colourless
Z = 4	0.42 × 0.31 × 0.19 mm
F(000) = 400

Data collection top

Bruker APEXII diffractometer	1234 independent reflections
Radiation source: fine-focus sealed tube	1207 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
phi and ϕ scans	θ_max = 60.0°, θ_min = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.749, T_max = 0.841	k = −7→8
3786 measured reflections	l = −5→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ²(F_o²) + (0.0766P)² + 0.2946P] where P = (F_o² + 2F_c²)/3
1234 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₉NO₃	V = 875.2 (3) Å³
M_r = 191.18	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.432 (2) Å	µ = 0.91 mm⁻¹
b = 7.6567 (14) Å	T = 293 K
c = 10.115 (2) Å	0.42 × 0.31 × 0.19 mm
β = 98.688 (7)°

Data collection top

Bruker APEXII diffractometer	1234 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1207 reflections with I > 2σ(I)
T_min = 0.749, T_max = 0.841	R_int = 0.028
3786 measured reflections	θ_max = 60.0°

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	Δρ_max = 0.16 e Å⁻³
1234 reflections	Δρ_min = −0.23 e Å⁻³
131 parameters

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 esds 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 > 2σ(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	0.91904 (12)	0.1492 (2)	0.88087 (15)	0.0436 (5)
O2	0.56202 (12)	−0.1251 (2)	0.82562 (16)	0.0482 (5)
O3	0.92280 (13)	−0.1661 (2)	0.43867 (15)	0.0454 (5)
N1	0.74293 (13)	0.0058 (2)	0.82293 (16)	0.0293 (5)
C1	0.74308 (15)	−0.0001 (2)	0.68070 (19)	0.0281 (6)
C2	0.83725 (16)	−0.0782 (2)	0.63281 (18)	0.0300 (6)
C3	0.83605 (17)	−0.0861 (3)	0.49542 (19)	0.0326 (6)
C4	0.74209 (18)	−0.0147 (3)	0.4099 (2)	0.0391 (7)
C5	0.64917 (18)	0.0627 (3)	0.4603 (2)	0.0407 (7)
C6	0.64839 (17)	0.0704 (3)	0.5970 (2)	0.0361 (6)
C7	0.65000 (16)	−0.0592 (2)	0.8850 (2)	0.0327 (6)
C8	0.68144 (17)	−0.0292 (3)	1.0320 (2)	0.0374 (7)
C9	0.80476 (18)	0.0493 (3)	1.0518 (2)	0.0367 (6)
C10	0.83298 (16)	0.0764 (2)	0.91334 (19)	0.0313 (6)
H2	0.90020	−0.12450	0.69140	0.0360*
H3	0.978 (3)	−0.223 (5)	0.502 (4)	0.088 (10)*
H4	0.74170	−0.01900	0.31800	0.0470*
H5	0.58650	0.11000	0.40200	0.0490*
H6	0.58570	0.12170	0.63140	0.0430*
H8A	0.68090	−0.13840	1.08050	0.0450*
H8B	0.62560	0.05040	1.06340	0.0450*
H9A	0.80610	0.15940	1.09940	0.0440*
H9B	0.86130	−0.02960	1.10190	0.0440*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0306 (8)	0.0573 (10)	0.0443 (9)	−0.0123 (7)	0.0103 (7)	−0.0083 (7)
O2	0.0306 (8)	0.0641 (10)	0.0501 (9)	−0.0141 (7)	0.0066 (7)	0.0068 (8)
O3	0.0417 (9)	0.0634 (10)	0.0328 (9)	0.0051 (7)	0.0110 (7)	−0.0054 (7)
N1	0.0224 (8)	0.0360 (9)	0.0305 (9)	−0.0012 (6)	0.0071 (6)	0.0000 (6)
C1	0.0248 (10)	0.0305 (10)	0.0290 (10)	−0.0052 (7)	0.0045 (8)	0.0009 (7)
C2	0.0248 (10)	0.0362 (11)	0.0283 (10)	−0.0014 (8)	0.0021 (8)	0.0010 (8)
C3	0.0302 (10)	0.0375 (11)	0.0304 (10)	−0.0074 (8)	0.0060 (8)	−0.0009 (8)
C4	0.0377 (12)	0.0478 (13)	0.0299 (10)	−0.0099 (9)	−0.0010 (9)	0.0044 (9)
C5	0.0308 (11)	0.0470 (13)	0.0406 (12)	−0.0039 (9)	−0.0067 (9)	0.0116 (9)
C6	0.0241 (10)	0.0386 (11)	0.0452 (12)	−0.0010 (8)	0.0043 (8)	0.0051 (9)
C7	0.0250 (10)	0.0340 (10)	0.0405 (11)	0.0024 (8)	0.0100 (9)	0.0054 (8)
C8	0.0349 (11)	0.0431 (12)	0.0371 (11)	0.0054 (8)	0.0151 (9)	0.0020 (8)
C9	0.0333 (11)	0.0447 (11)	0.0333 (11)	0.0060 (9)	0.0085 (8)	−0.0043 (9)
C10	0.0250 (10)	0.0345 (11)	0.0353 (11)	0.0028 (8)	0.0072 (8)	−0.0048 (8)

Geometric parameters (Å, º) top

O1—C10	1.218 (2)	C5—C6	1.385 (3)
O2—C7	1.202 (2)	C7—C8	1.494 (3)
O3—C3	1.364 (3)	C8—C9	1.518 (3)
O3—H3	0.94 (4)	C9—C10	1.498 (3)
N1—C1	1.440 (2)	C2—H2	0.9300
N1—C7	1.404 (2)	C4—H4	0.9300
N1—C10	1.380 (2)	C5—H5	0.9300
C1—C2	1.382 (2)	C6—H6	0.9300
C1—C6	1.380 (3)	C8—H8A	0.9700
C2—C3	1.389 (3)	C8—H8B	0.9700
C3—C4	1.386 (3)	C9—H9A	0.9700
C4—C5	1.380 (3)	C9—H9B	0.9700

C3—O3—H3	112 (2)	N1—C10—C9	108.71 (16)
C1—N1—C10	124.14 (15)	O1—C10—N1	123.55 (18)
C7—N1—C10	112.43 (16)	C1—C2—H2	121.00
C1—N1—C7	123.43 (15)	C3—C2—H2	121.00
N1—C1—C6	118.80 (16)	C3—C4—H4	120.00
C2—C1—C6	122.34 (18)	C5—C4—H4	120.00
N1—C1—C2	118.85 (16)	C4—C5—H5	120.00
C1—C2—C3	118.63 (17)	C6—C5—H5	120.00
O3—C3—C4	117.31 (17)	C1—C6—H6	121.00
C2—C3—C4	119.80 (18)	C5—C6—H6	121.00
O3—C3—C2	122.87 (18)	C7—C8—H8A	111.00
C3—C4—C5	120.42 (19)	C7—C8—H8B	111.00
C4—C5—C6	120.57 (19)	C9—C8—H8A	111.00
C1—C6—C5	118.24 (19)	C9—C8—H8B	111.00
O2—C7—N1	123.91 (18)	H8A—C8—H8B	109.00
N1—C7—C8	107.82 (16)	C8—C9—H9A	111.00
O2—C7—C8	128.27 (18)	C8—C9—H9B	111.00
C7—C8—C9	105.74 (16)	C10—C9—H9A	111.00
C8—C9—C10	104.97 (16)	C10—C9—H9B	111.00
O1—C10—C9	127.74 (18)	H9A—C9—H9B	109.00

C7—N1—C1—C2	−125.04 (18)	N1—C1—C2—C3	178.96 (16)
C10—N1—C1—C2	55.4 (2)	C2—C1—C6—C5	−0.4 (3)
C7—N1—C1—C6	54.1 (2)	C1—C2—C3—C4	0.7 (3)
C10—N1—C1—C6	−125.46 (19)	C1—C2—C3—O3	−177.55 (17)
C7—N1—C10—C9	3.7 (2)	C2—C3—C4—C5	−0.6 (3)
C1—N1—C10—O1	4.0 (3)	O3—C3—C4—C5	177.7 (2)
C7—N1—C10—O1	−175.62 (16)	C3—C4—C5—C6	0.1 (3)
C1—N1—C7—O2	−0.3 (3)	C4—C5—C6—C1	0.4 (3)
C10—N1—C7—C8	−0.1 (2)	O2—C7—C8—C9	177.14 (19)
C10—N1—C7—O2	179.37 (17)	N1—C7—C8—C9	−3.4 (2)
C1—N1—C10—C9	−176.69 (16)	C7—C8—C9—C10	5.3 (2)
C1—N1—C7—C8	−179.75 (16)	C8—C9—C10—O1	173.70 (18)
C6—C1—C2—C3	−0.2 (3)	C8—C9—C10—N1	−5.6 (2)
N1—C1—C6—C5	−179.51 (18)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.94 (4)	1.82 (4)	2.758 (2)	175 (4)
C8—H8A···Cgⁱⁱ	0.97	2.83	3.613 (3)	138
C9—H9A···Cgⁱⁱ	0.97	2.79	3.579 (3)	139

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.94 (4)	1.82 (4)	2.758 (2)	175 (4)
C8—H8A···Cgⁱⁱ	0.97	2.83	3.613 (3)	138
C9—H9A···Cgⁱⁱ	0.97	2.79	3.579 (3)	139

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

Acknowledgements

The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, India, for the data collection.

References

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Page o927

doi:10.1107/S1600536814016328

Open

access