2-Ethyl­isoindoline-1,3-dione

The title compound, C₁₀H₉NO₂, was synthesized by mixing phthalic anhydride, ethanamine and triethyl­amine in toluene. The phthalimide unit is essentially planar. The crystal structure is stabilized by weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.045
• wR factor = 0.113
• Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.28
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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           25.02
           From the CIF: _reflns_number_total                866
           Count of symmetry unique reflns          872
           Completeness (_total/calc)             99.31%
           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
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   2 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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-Ethylisoindoline-1,3-dione

Crystal data

C10H9NO2	F(000) = 184
Mr = 175.18	Dx = 1.343 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2yb	Cell parameters from 626 reflections
a = 7.254 (6) Å	θ = 2.8–22.0°
b = 4.475 (4) Å	µ = 0.10 mm^−1
c = 13.506 (10) Å	T = 294 K
β = 98.774 (13)°	Plate, colourless
V = 433.3 (6) Å^3	0.32 × 0.26 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	866 independent reflections
Radiation source: fine-focus sealed tube	617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→8
Tmin = 0.970, Tmax = 0.981	k = −5→5
2113 measured reflections	l = −16→10

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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.0312P] where P = (Fo^2 + 2Fc^2)/3
866 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.14 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3
36 constraints

Special details

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	0.1922 (4)	0.5069 (8)	0.59624 (19)	0.0711 (10)
O2	−0.1763 (4)	0.5194 (8)	0.83740 (18)	0.0660 (11)
N1	−0.0229 (4)	0.5609 (8)	0.70237 (19)	0.0434 (8)
C1	0.1396 (5)	0.4466 (11)	0.6737 (3)	0.0464 (10)
C2	0.2223 (5)	0.2533 (10)	0.7558 (3)	0.0438 (11)
C3	0.3811 (6)	0.0878 (12)	0.7669 (3)	0.0600 (12)
H3	0.4564	0.0819	0.7170	0.072*
C4	0.4268 (6)	−0.0721 (12)	0.8551 (4)	0.0671 (14)
H4	0.5339	−0.1894	0.8644	0.080*
C5	0.3173 (6)	−0.0600 (11)	0.9283 (3)	0.0619 (13)
H5	0.3520	−0.1660	0.9875	0.074*
C6	0.1570 (6)	0.1058 (11)	0.9163 (3)	0.0525 (11)
H6	0.0811	0.1115	0.9659	0.063*
C7	0.1117 (5)	0.2623 (10)	0.8294 (2)	0.0393 (9)
C8	−0.0466 (5)	0.4542 (9)	0.7959 (3)	0.0447 (11)
C9	−0.1505 (6)	0.7572 (11)	0.6414 (3)	0.0556 (12)
H9A	−0.0840	0.8635	0.5952	0.067*
H9B	−0.1980	0.9037	0.6840	0.067*
C10	−0.3102 (6)	0.5921 (14)	0.5835 (3)	0.0704 (14)
H10A	−0.2646	0.4575	0.5375	0.106*
H10B	−0.3951	0.7318	0.5470	0.106*
H10C	−0.3738	0.4806	0.6288	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.079 (2)	0.084 (3)	0.0561 (16)	−0.005 (2)	0.0301 (15)	0.0097 (19)
O2	0.0536 (16)	0.086 (3)	0.0638 (16)	0.021 (2)	0.0250 (15)	0.004 (2)
N1	0.0425 (18)	0.047 (2)	0.0410 (16)	0.003 (2)	0.0044 (14)	0.0042 (18)
C1	0.045 (2)	0.049 (3)	0.045 (2)	−0.008 (2)	0.0075 (18)	−0.002 (2)
C2	0.038 (2)	0.041 (2)	0.053 (2)	−0.006 (2)	0.009 (2)	−0.007 (2)
C3	0.042 (2)	0.063 (3)	0.076 (3)	−0.001 (3)	0.015 (2)	−0.009 (3)
C4	0.045 (2)	0.055 (3)	0.097 (3)	0.010 (3)	−0.004 (3)	−0.012 (3)
C5	0.061 (3)	0.055 (3)	0.065 (3)	0.004 (3)	−0.007 (2)	0.003 (3)
C6	0.055 (3)	0.053 (3)	0.050 (2)	−0.006 (3)	0.0090 (19)	−0.002 (2)
C7	0.037 (2)	0.042 (2)	0.0392 (19)	−0.001 (2)	0.0054 (17)	0.000 (2)
C8	0.041 (2)	0.048 (3)	0.045 (2)	0.005 (2)	0.0034 (18)	−0.006 (2)
C9	0.060 (3)	0.050 (3)	0.055 (2)	0.008 (3)	0.002 (2)	0.010 (3)
C10	0.056 (3)	0.075 (3)	0.073 (3)	−0.004 (3)	−0.013 (2)	0.015 (3)

Geometric parameters (Å, º)

O1—C1	1.198 (4)	C5—C6	1.367 (6)
O2—C8	1.203 (4)	C5—H5	0.9300
N1—C8	1.385 (4)	C6—C7	1.364 (5)
N1—C1	1.393 (5)	C6—H6	0.9300
N1—C9	1.440 (5)	C7—C8	1.450 (5)
C1—C2	1.461 (6)	C9—C10	1.491 (6)
C2—C3	1.358 (6)	C9—H9A	0.9700
C2—C7	1.369 (5)	C9—H9B	0.9700
C3—C4	1.387 (6)	C10—H10A	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.362 (6)	C10—H10C	0.9600
C4—H4	0.9300
C8—N1—C1	110.8 (3)	C5—C6—H6	121.0
C8—N1—C9	125.0 (3)	C6—C7—C2	121.3 (4)
C1—N1—C9	124.2 (3)	C6—C7—C8	130.4 (3)
O1—C1—N1	123.7 (4)	C2—C7—C8	108.3 (3)
O1—C1—C2	130.4 (4)	O2—C8—N1	123.8 (4)
N1—C1—C2	105.9 (3)	O2—C8—C7	129.6 (3)
C3—C2—C7	121.2 (4)	N1—C8—C7	106.6 (3)
C3—C2—C1	130.5 (4)	N1—C9—C10	112.2 (4)
C7—C2—C1	108.3 (4)	N1—C9—H9A	109.2
C2—C3—C4	117.6 (4)	C10—C9—H9A	109.2
C2—C3—H3	121.2	N1—C9—H9B	109.2
C4—C3—H3	121.2	C10—C9—H9B	109.2
C5—C4—C3	120.9 (4)	H9A—C9—H9B	107.9
C5—C4—H4	119.5	C9—C10—H10A	109.5
C3—C4—H4	119.5	C9—C10—H10B	109.5
C4—C5—C6	121.1 (4)	H10A—C10—H10B	109.5
C4—C5—H5	119.5	C9—C10—H10C	109.5
C6—C5—H5	119.5	H10A—C10—H10C	109.5
C7—C6—C5	118.0 (4)	H10B—C10—H10C	109.5
C7—C6—H6	121.0
C8—N1—C1—O1	−179.4 (4)	C3—C2—C7—C6	0.1 (6)
C9—N1—C1—O1	2.1 (6)	C1—C2—C7—C6	−178.9 (4)
C8—N1—C1—C2	0.2 (4)	C3—C2—C7—C8	−179.6 (4)
C9—N1—C1—C2	−178.3 (4)	C1—C2—C7—C8	1.4 (4)
O1—C1—C2—C3	−0.3 (8)	C1—N1—C8—O2	−180.0 (4)
N1—C1—C2—C3	−179.9 (4)	C9—N1—C8—O2	−1.5 (6)
O1—C1—C2—C7	178.6 (5)	C1—N1—C8—C7	0.6 (4)
N1—C1—C2—C7	−1.0 (4)	C9—N1—C8—C7	179.1 (4)
C7—C2—C3—C4	0.1 (6)	C6—C7—C8—O2	−0.3 (7)
C1—C2—C3—C4	178.8 (4)	C2—C7—C8—O2	179.4 (4)
C2—C3—C4—C5	−0.7 (7)	C6—C7—C8—N1	179.0 (4)
C3—C4—C5—C6	1.2 (7)	C2—C7—C8—N1	−1.2 (4)
C4—C5—C6—C7	−0.9 (7)	C8—N1—C9—C10	−82.1 (5)
C5—C6—C7—C2	0.3 (6)	C1—N1—C9—C10	96.2 (5)
C5—C6—C7—C8	180.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^i	0.93	2.55	3.449 (6)	164

Symmetry code: (i) x+1, y−1, z.