Crystal structure of N-(3-hy­droxy­phenyl)succinimide

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).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.140
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5616
PLAT023_ALERT_3_B Resolution (too) Low [sin(theta)/Lambda < 0.6]..      59.98 Degree
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......      0.947 Note
PLAT939_ALERT_3_B Large Value of Not (SHELXL) Weight Optimized S .     221.93

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5616
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.4198
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.42 Note
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.287 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.562         69 Why ?
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         13 Note
PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) .          1 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          95 %
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   3 ALERT level A = Most likely a serious problem - resolve or explain
   4 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   6 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
  12 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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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. Experimental

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).

Related literature

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

Computing details

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

	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

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) Å^3	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 F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0766P)^2 + 0.2946P] where P = (Fo^2 + 2Fc^2)/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)

	U^11	U^22	U^33	U^12	U^13	U^23
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···O1^i	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) −x+2, y−1/2, −z+3/2; (ii) x, −y+3/2, z+1/2.