Crystal structure of N-(3-hy­droxy­phenyl)succinimide

Abstract

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).

Related literature  

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

Experimental  

Crystal data  

• C₁₀H₉NO₃

• M _r = 191.18

• Monoclinic,

• a = 11.432 (2) Å

• b = 7.6567 (14) Å

• c = 10.115 (2) Å

• β = 98.688 (7)°

• V = 875.2 (3) ų

• Z = 4

• Cu Kα radiation

• μ = 0.91 mm⁻¹

• T = 293 K

• 0.42 × 0.31 × 0.19 mm

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°

Refinement  

• R[F ² > 2σ(F ²)] = 0.044

• wR(F ²) = 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

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.

Supplementary Material

CCDC reference: 1013858

Additional supporting information: crystallographic information; 3D view; checkCIF report

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⋯Cg ii	0.97	2.83	3.613 (3)	138
C9—H9A⋯Cg ii	0.97	2.79	3.579 (3)	139

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

S1. Introduction

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.

S2.1. Synthesis and crystallization

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.

S2.2. Refinement

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).

S3. Results and discussion

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).

Figures

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).

Crystal data

C10H9NO3	Prism
Mr = 191.18	Dx = 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

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

Refinement

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(Fo2) + (0.0766P)2 + 0.2946P] where P = (Fo2 + 2Fc2)/3
1234 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)

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.