1-Oxo-N-phenyl­isoindoline-2-carbox­amide

The title mol­ecule, C₁₅H₁₂N₂O₂, is essentially planar. The crystal structure is stabilized by an extensive hydrogen-bonded network. There are two intra­molecular hydrogen bonds resulting in six-membered rings in graph-set patterns S(6) and three inter­molecular inter­actions. Two of these are C—H...O inter­molecular hydrogen bonds that result in dimers, representing R₂²(10) graph-set patterns, and a C—H...N hydrogen bond leading to the formation of chains of mol­ecules along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.097
• Data-to-parameter ratio = 16.1

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S1. Comment

Isoindole type compounds are important as intermediates for the synthesis of novel multidrugs resistance reversal agents (Berger et al., 1999). They have also shown diuretic activity (Cignarella et al., 1981). Several isoindoles have exhibited anti-inflammatory and analgesic activity (Mancilla et al., 2007). In our efforts to isolate chromagens responsible for color development in the reaction of N-phenylurea with ortho phthaldehyde (OPTA), the title compound, (I), was prepared, the crystal structure of which is presented in this article.

The structure of (I) is composed of an essentially planar molecule comprised of an isoindole ring that is briged through a carboxamide group to a phenyl ring (Fig. 1). A mean-planes calculation through all non-hydrogen atoms revealed that C12 and N1 atoms lie 0.057 (1) and 0.052 (1) Å above and below, respectively, from the plane. The angle between mean-planes of the isoindole ring and the phenyl ring is 2.62 (8)°. The structure is stabilized by two intramolecular hydrogen bonds N2—H2N···O1 and C11—H11A···O2 that result in six membered rings which may be best defined in graph set patterns S(6) (Bernstein et al., 1994); details of hydrogen bonding geometry have been provided in the Table. In addition, rather weak intermolecular interactions of two distinct types are present in the crystal (Fig. 2). The C—H···O type intermolecular H-bonding results in dimers forming ten-membered rings ···O1—C8—C1—C2—H2···O1ⁱ and ···O2—C9—N1—C7—H7b···O2ⁱⁱ, both representing R₂²(10) graph set patterns (Bernstein et al., 1994). The C—H···N type H-bonding results in chains of molecules in a pattern ···N2—C9—N1—C7—H7B···N2ⁱⁱⁱ along the b-aixs. Symmetry codes as in the bydrogen bond geometry table.

The structure of 2-(bis(1-oxo-2,3-dihydroisoindol-2-yl)methyl)tetrahydrothiophene (Benati et al., 2003) which is somewhat related to the title compound has been reported.

Related literature

For related literature, see: Benati et al. (2003); Berger et al. (1999); Bernstein et al. (1994); Cignarella et al. (1981); Mancilla et al. (2007).

S2. Experimental

A mixture of o-phthaldehyde (0.67 g, 200 mmol) and N-phenylurea (0.68 g, 200 mmol) in 100 ml of ethanol was refluxed for 12 hrs. The contents of flask were then left to stand for 48 hrs. at room temperature. The crystals of (I) thus formed were filtered, washed with hexane, ether and ethanol and were dried at room temperature. Crystals suitable for X-ray diffraction were grown from a solution of acetone by slow evaporation at room temperature.

S3. Refinement

H-atoms were included in the refinements at geometrically idealized positions with C—H_aromatic = 0.95, CH₂ = 0.99 and N—H = 0.88 Å and U_iso = 1.2 times U_eq of the atoms to which they were bonded. The final difference map was free of any chemically significant features.

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. The molecular structure with displacement ellipsoids plotted at 50% probability level; intermolecular interactions have been indicated by broken lines.
	Fig. 2. H-bonding interactions in the unit cell of (I); H-atoms not involved in interactions have been ignored. H-bonds are shown as dashed lines.

1-Oxo-N-phenylisoindoline-2-carboxamide

Crystal data

C15H12N2O2	F(000) = 528
Mr = 252.27	Dx = 1.378 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5034 reflections
a = 12.905 (4) Å	θ = 2.6–27.5°
b = 5.619 (1) Å	µ = 0.09 mm^−1
c = 17.161 (6) Å	T = 173 K
β = 102.228 (17)°	Needle, colorless
V = 1216.2 (6) Å^3	0.35 × 0.10 × 0.06 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2768 independent reflections
Radiation source: fine-focus sealed tube	2119 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and ϕ scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −16→16
Tmin = 0.968, Tmax = 0.994	k = −6→7
5034 measured reflections	l = −22→22

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 0.39P] where P = (Fo^2 + 2Fc^2)/3
2768 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. IR spectra (nujol) showed vibrations 3425 cm^-1 (N—H), 1714 and 1680 cm^-1 (C=O), 1600 and 155.8 cm^-1 (C=C), 1150 cm^-1 (C—O). ¹H-NMR (DMSO-d₆); δ: 4.92 (s –CH₂–), 7.10–7.93 (aromatic ring protons, 9H), 10.72 (s, NH). ¹³C-NMR (DMSO-d₆); δ: 48.59 (–CH₂–), 123.37 (C₄), 124.08 (C₃), 128.65 (C₅), 130.94 (C₆), 133.93 (C₂), 141.07 (C₁), 150.25 (C₉), 169.44 (C₈) and 120.06, 124.86, 129.03, 137.50 (N—Ph carbons). Anal. Calcd for C₁₅H₁₂N₂O₂. Required: C, 71.42; H, 4.79; N, 11.0; O, 12.68; Found: C, 71.40; H, 4.80; N, 11.07; O, 12.70. m.p. 441 K. m/z; 252.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.92562 (7)	−0.27832 (16)	0.39885 (5)	0.0328 (2)
O2	0.89390 (8)	0.31349 (17)	0.24855 (6)	0.0406 (3)
N1	0.97796 (8)	0.07840 (18)	0.34984 (6)	0.0263 (2)
N2	0.80821 (8)	−0.01677 (19)	0.28210 (6)	0.0297 (3)
H2N	0.8169	−0.1366	0.3159	0.036*
C1	1.09874 (10)	−0.1015 (2)	0.44905 (7)	0.0268 (3)
C2	1.14801 (11)	−0.2514 (2)	0.51004 (8)	0.0315 (3)
H2	1.1139	−0.3908	0.5234	0.038*
C3	1.24880 (11)	−0.1894 (3)	0.55062 (8)	0.0356 (3)
H3	1.2846	−0.2866	0.5932	0.043*
C4	1.29830 (11)	0.0143 (3)	0.52972 (8)	0.0380 (3)
H4	1.3676	0.0532	0.5584	0.046*
C5	1.24877 (11)	0.1619 (2)	0.46793 (8)	0.0346 (3)
H5	1.2834	0.2991	0.4535	0.041*
C6	1.14717 (10)	0.1021 (2)	0.42818 (7)	0.0281 (3)
C7	1.07353 (10)	0.2269 (2)	0.36116 (8)	0.0296 (3)
H7A	1.0587	0.3916	0.3761	0.036*
H7B	1.1030	0.2308	0.3124	0.036*
C8	0.99162 (10)	−0.1207 (2)	0.39860 (7)	0.0263 (3)
C9	0.89044 (10)	0.1374 (2)	0.28902 (7)	0.0284 (3)
C10	0.71058 (10)	−0.0067 (2)	0.22699 (8)	0.0301 (3)
C11	0.68394 (11)	0.1681 (3)	0.16870 (8)	0.0360 (3)
H11	0.7324	0.2927	0.1648	0.043*
C12	0.58577 (11)	0.1588 (3)	0.11620 (9)	0.0419 (4)
H12	0.5675	0.2784	0.0765	0.050*
C13	0.51455 (12)	−0.0206 (3)	0.12064 (9)	0.0452 (4)
H13	0.4481	−0.0259	0.0840	0.054*
C14	0.54067 (12)	−0.1927 (3)	0.17890 (10)	0.0480 (4)
H14	0.4916	−0.3158	0.1828	0.058*
C15	0.63785 (11)	−0.1869 (3)	0.23162 (9)	0.0401 (3)
H15	0.6552	−0.3067	0.2713	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0361 (5)	0.0257 (5)	0.0383 (5)	−0.0031 (4)	0.0116 (4)	0.0042 (4)
O2	0.0453 (6)	0.0332 (5)	0.0402 (6)	−0.0068 (4)	0.0016 (4)	0.0125 (4)
N1	0.0310 (6)	0.0215 (5)	0.0280 (5)	−0.0004 (4)	0.0093 (4)	0.0015 (4)
N2	0.0330 (6)	0.0276 (5)	0.0290 (6)	−0.0025 (4)	0.0080 (4)	0.0037 (4)
C1	0.0315 (6)	0.0226 (6)	0.0286 (6)	0.0032 (5)	0.0119 (5)	−0.0018 (5)
C2	0.0375 (7)	0.0267 (6)	0.0328 (7)	0.0051 (5)	0.0131 (6)	0.0026 (5)
C3	0.0383 (7)	0.0360 (7)	0.0333 (7)	0.0105 (6)	0.0094 (6)	0.0028 (6)
C4	0.0322 (7)	0.0410 (8)	0.0398 (8)	0.0035 (6)	0.0054 (6)	−0.0033 (6)
C5	0.0349 (7)	0.0296 (7)	0.0403 (8)	−0.0023 (6)	0.0105 (6)	−0.0016 (6)
C6	0.0330 (7)	0.0237 (6)	0.0296 (7)	0.0019 (5)	0.0113 (5)	−0.0023 (5)
C7	0.0336 (7)	0.0223 (6)	0.0336 (7)	−0.0033 (5)	0.0084 (5)	0.0006 (5)
C8	0.0340 (7)	0.0200 (6)	0.0281 (6)	0.0025 (5)	0.0139 (5)	−0.0004 (5)
C9	0.0347 (7)	0.0248 (6)	0.0272 (6)	0.0002 (5)	0.0097 (5)	−0.0012 (5)
C10	0.0314 (7)	0.0302 (6)	0.0302 (7)	0.0011 (5)	0.0100 (5)	−0.0036 (5)
C11	0.0335 (7)	0.0347 (7)	0.0406 (8)	−0.0003 (6)	0.0092 (6)	0.0050 (6)
C12	0.0356 (7)	0.0448 (8)	0.0444 (8)	0.0033 (6)	0.0067 (6)	0.0085 (7)
C13	0.0339 (8)	0.0493 (9)	0.0494 (9)	−0.0019 (7)	0.0024 (7)	0.0009 (7)
C14	0.0407 (8)	0.0425 (8)	0.0583 (10)	−0.0122 (7)	0.0048 (7)	0.0028 (7)
C15	0.0419 (8)	0.0341 (7)	0.0434 (8)	−0.0063 (6)	0.0070 (7)	0.0043 (6)

Geometric parameters (Å, º)

O1—C8	1.2293 (15)	C5—C6	1.3851 (19)
O2—C9	1.2148 (16)	C5—H5	0.9500
N1—C8	1.3859 (15)	C6—C7	1.5016 (18)
N1—C9	1.4057 (17)	C7—H7A	0.9900
N1—C7	1.4676 (16)	C7—H7B	0.9900
N2—C9	1.3556 (16)	C10—C11	1.3921 (19)
N2—C10	1.4073 (17)	C10—C15	1.3944 (19)
N2—H2N	0.8800	C11—C12	1.391 (2)
C1—C6	1.3865 (17)	C11—H11	0.9500
C1—C2	1.3883 (18)	C12—C13	1.377 (2)
C1—C8	1.4715 (18)	C12—H12	0.9500
C2—C3	1.384 (2)	C13—C14	1.380 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.394 (2)	C14—C15	1.383 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.391 (2)	C15—H15	0.9500
C4—H4	0.9500
C8—N1—C9	128.19 (10)	N1—C7—H7B	111.3
C8—N1—C7	112.54 (10)	C6—C7—H7B	111.3
C9—N1—C7	118.99 (10)	H7A—C7—H7B	109.2
C9—N2—C10	127.29 (11)	O1—C8—N1	125.74 (12)
C9—N2—H2N	116.4	O1—C8—C1	128.03 (11)
C10—N2—H2N	116.4	N1—C8—C1	106.22 (10)
C6—C1—C2	122.40 (12)	O2—C9—N2	126.40 (12)
C6—C1—C8	109.11 (11)	O2—C9—N1	119.71 (12)
C2—C1—C8	128.47 (12)	N2—C9—N1	113.89 (11)
C3—C2—C1	117.27 (12)	C11—C10—C15	119.12 (13)
C3—C2—H2	121.4	C11—C10—N2	124.12 (12)
C1—C2—H2	121.4	C15—C10—N2	116.75 (12)
C2—C3—C4	120.69 (13)	C12—C11—C10	119.41 (13)
C2—C3—H3	119.7	C12—C11—H11	120.3
C4—C3—H3	119.7	C10—C11—H11	120.3
C5—C4—C3	121.61 (13)	C13—C12—C11	121.24 (14)
C5—C4—H4	119.2	C13—C12—H12	119.4
C3—C4—H4	119.2	C11—C12—H12	119.4
C6—C5—C4	117.71 (13)	C12—C13—C14	119.29 (14)
C6—C5—H5	121.1	C12—C13—H13	120.4
C4—C5—H5	121.1	C14—C13—H13	120.4
C5—C6—C1	120.30 (12)	C13—C14—C15	120.41 (14)
C5—C6—C7	130.05 (12)	C13—C14—H14	119.8
C1—C6—C7	109.66 (11)	C15—C14—H14	119.8
N1—C7—C6	102.34 (10)	C14—C15—C10	120.52 (14)
N1—C7—H7A	111.3	C14—C15—H15	119.7
C6—C7—H7A	111.3	C10—C15—H15	119.7
C6—C1—C2—C3	0.42 (18)	C2—C1—C8—O1	−2.6 (2)
C8—C1—C2—C3	−177.84 (12)	C6—C1—C8—N1	−1.61 (13)
C1—C2—C3—C4	−0.79 (19)	C2—C1—C8—N1	176.84 (12)
C2—C3—C4—C5	0.1 (2)	C10—N2—C9—O2	0.3 (2)
C3—C4—C5—C6	1.0 (2)	C10—N2—C9—N1	−179.59 (11)
C4—C5—C6—C1	−1.35 (19)	C8—N1—C9—O2	−175.71 (12)
C4—C5—C6—C7	178.64 (13)	C7—N1—C9—O2	−2.24 (17)
C2—C1—C6—C5	0.67 (19)	C8—N1—C9—N2	4.20 (17)
C8—C1—C6—C5	179.23 (11)	C7—N1—C9—N2	177.67 (10)
C2—C1—C6—C7	−179.32 (11)	C9—N2—C10—C11	0.9 (2)
C8—C1—C6—C7	−0.76 (13)	C9—N2—C10—C15	−179.93 (12)
C8—N1—C7—C6	−3.79 (13)	C15—C10—C11—C12	−0.3 (2)
C9—N1—C7—C6	−178.24 (10)	N2—C10—C11—C12	178.82 (13)
C5—C6—C7—N1	−177.34 (13)	C10—C11—C12—C13	−0.2 (2)
C1—C6—C7—N1	2.65 (13)	C11—C12—C13—C14	0.8 (2)
C9—N1—C8—O1	−3.3 (2)	C12—C13—C14—C15	−0.8 (3)
C7—N1—C8—O1	−177.10 (12)	C13—C14—C15—C10	0.3 (2)
C9—N1—C8—C1	177.28 (11)	C11—C10—C15—C14	0.2 (2)
C7—N1—C8—C1	3.46 (13)	N2—C10—C15—C14	−178.95 (13)
C6—C1—C8—O1	178.97 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.95	2.41	3.3105 (17)	159
C7—H7B···O2^ii	0.99	2.57	3.0746 (17)	112
C7—H7B···N2^iii	0.99	2.60	3.4695 (18)	147
C11—H11···O2	0.95	2.27	2.8833 (19)	122
N2—H2N···O1	0.88	1.95	2.6803 (15)	140

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