3-(4-Ethyl­anilino)isobenzofuran-1(3H)-one

Crystals of the title compound, C₁₆H₁₅NO₂, are stabilized by inter­molecular N—H...O and C—H...O hydrogen bonds. The N—H...O hydrogen bonds generate C(6) chains along the c axis; these chains are further connected by C—H...O hydrogen bonds, forming R₄⁴(21) motifs and a three-dimensional network. The phthalide group is planar and the dihedral angle between it and the benzene ring is 68.75 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.115
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.69 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(4-ethylanilino)isobenzofuran-1(3H)-one

Crystal data

C16H15NO2	F(000) = 536
Mr = 253.29	Dx = 1.243 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11974 reflections
a = 7.8823 (6) Å	θ = 1.6–27.1°
b = 24.8672 (14) Å	µ = 0.08 mm^−1
c = 7.1265 (5) Å	T = 296 K
β = 104.261 (6)°	Prismatic plate, colorless
V = 1353.82 (16) Å^3	0.69 × 0.46 × 0.07 mm
Z = 4

Data collection

Stoe IPDSII diffractometer	2667 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1800 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.061
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −30→30
Tmin = 0.956, Tmax = 0.994	l = −8→8
13077 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0644P)^2 + 0.0208P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2667 reflections	Δρmax = 0.12 e Å^−3
177 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (3)

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
C1	0.15904 (18)	0.22920 (6)	0.4231 (2)	0.0573 (3)
C2	−0.01376 (16)	0.24783 (6)	0.31597 (19)	0.0557 (3)
C3	−0.15986 (18)	0.21837 (7)	0.2225 (2)	0.0648 (4)
H3	−0.1571	0.1810	0.2183	0.078*
C4	−0.30810 (19)	0.24645 (8)	0.1367 (2)	0.0734 (4)
H4	−0.4081	0.2279	0.0727	0.088*
C5	−0.31132 (19)	0.30193 (8)	0.1438 (2)	0.0778 (5)
H5	−0.4139	0.3200	0.0848	0.093*
C6	−0.16579 (19)	0.33136 (7)	0.2364 (2)	0.0718 (4)
H6	−0.1685	0.3687	0.2396	0.086*
C7	−0.01643 (16)	0.30313 (6)	0.3239 (2)	0.0583 (4)
C8	0.15514 (17)	0.32300 (6)	0.4447 (2)	0.0599 (4)
H8	0.1361	0.3395	0.5628	0.072*
C9	0.39267 (18)	0.38720 (6)	0.4500 (2)	0.0635 (4)
C10	0.4801 (2)	0.41826 (7)	0.3433 (3)	0.0774 (5)
H10	0.4395	0.4198	0.2093	0.093*
C11	0.6280 (2)	0.44711 (7)	0.4342 (3)	0.0877 (5)
H11	0.6852	0.4677	0.3596	0.105*
C12	0.6924 (2)	0.44612 (6)	0.6317 (3)	0.0833 (6)
C13	0.6034 (2)	0.41554 (7)	0.7354 (3)	0.0858 (5)
H13	0.6435	0.4145	0.8695	0.103*
C14	0.4558 (2)	0.38600 (7)	0.6485 (3)	0.0778 (5)
H14	0.3994	0.3654	0.7238	0.093*
C15	0.8565 (2)	0.47707 (8)	0.7286 (4)	0.1087 (7)
H15A	0.8635	0.5091	0.6534	0.130*
H15B	0.8475	0.4885	0.8560	0.130*
C16	1.0191 (3)	0.44560 (9)	0.7491 (4)	0.1249 (9)
H16A	1.0310	0.4351	0.6233	0.150*
H16B	1.0142	0.4141	0.8252	0.150*
H16C	1.1178	0.4672	0.8120	0.150*
N1	0.23987 (16)	0.35993 (5)	0.3520 (2)	0.0666 (4)
O1	0.21509 (13)	0.18377 (4)	0.44866 (14)	0.0686 (3)
O2	0.25695 (11)	0.27195 (4)	0.49744 (15)	0.0637 (3)
H1	0.235 (2)	0.3522 (7)	0.223 (3)	0.093 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0500 (7)	0.0659 (9)	0.0549 (7)	0.0018 (6)	0.0110 (6)	0.0003 (6)
C2	0.0436 (7)	0.0681 (9)	0.0553 (7)	−0.0007 (6)	0.0116 (6)	−0.0001 (6)
C3	0.0506 (8)	0.0781 (10)	0.0654 (8)	−0.0097 (7)	0.0135 (7)	−0.0019 (7)
C4	0.0441 (7)	0.1030 (13)	0.0696 (9)	−0.0111 (8)	0.0075 (7)	−0.0018 (8)
C5	0.0451 (7)	0.1059 (14)	0.0770 (10)	0.0114 (8)	0.0050 (7)	0.0100 (9)
C6	0.0566 (8)	0.0758 (10)	0.0785 (10)	0.0114 (7)	0.0083 (8)	0.0049 (7)
C7	0.0456 (7)	0.0685 (9)	0.0592 (7)	0.0038 (6)	0.0099 (6)	−0.0009 (6)
C8	0.0505 (7)	0.0611 (8)	0.0653 (8)	0.0029 (6)	0.0090 (6)	−0.0036 (6)
C9	0.0555 (8)	0.0541 (8)	0.0792 (9)	0.0015 (6)	0.0133 (7)	−0.0053 (6)
C10	0.0730 (10)	0.0704 (10)	0.0906 (11)	−0.0052 (8)	0.0236 (9)	−0.0045 (8)
C11	0.0753 (11)	0.0703 (11)	0.1232 (16)	−0.0126 (8)	0.0355 (11)	−0.0065 (10)
C12	0.0625 (9)	0.0614 (10)	0.1214 (16)	−0.0040 (7)	0.0141 (10)	−0.0155 (9)
C13	0.0733 (10)	0.0794 (11)	0.0931 (12)	−0.0086 (9)	−0.0011 (9)	−0.0083 (9)
C14	0.0676 (9)	0.0771 (10)	0.0820 (10)	−0.0109 (8)	0.0059 (8)	0.0002 (8)
C15	0.0750 (11)	0.0788 (12)	0.164 (2)	−0.0151 (9)	0.0129 (13)	−0.0251 (12)
C16	0.0732 (12)	0.1037 (16)	0.185 (3)	−0.0116 (11)	0.0078 (14)	−0.0219 (15)
N1	0.0603 (7)	0.0698 (8)	0.0671 (8)	−0.0097 (6)	0.0106 (6)	−0.0040 (6)
O1	0.0651 (6)	0.0680 (7)	0.0698 (6)	0.0104 (5)	0.0108 (5)	0.0039 (5)
O2	0.0456 (5)	0.0677 (6)	0.0706 (6)	0.0021 (4)	0.0009 (5)	−0.0025 (5)

Geometric parameters (Å, º)

C1—O1	1.2103 (16)	C9—C10	1.381 (2)
C1—O2	1.3435 (16)	C9—N1	1.4083 (18)
C1—C2	1.4631 (18)	C10—C11	1.386 (2)
C2—C7	1.377 (2)	C10—H10	0.9300
C2—C3	1.3889 (19)	C11—C12	1.373 (3)
C3—C4	1.369 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.368 (3)
C4—C5	1.381 (3)	C12—C15	1.517 (2)
C4—H4	0.9300	C13—C14	1.386 (2)
C5—C6	1.384 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.3806 (19)	C15—C16	1.478 (3)
C6—H6	0.9300	C15—H15A	0.9700
C7—C8	1.4967 (18)	C15—H15B	0.9700
C8—N1	1.3939 (19)	C16—H16A	0.9600
C8—O2	1.4993 (16)	C16—H16B	0.9600
C8—H8	0.9800	C16—H16C	0.9600
C9—C14	1.379 (2)	N1—H1	0.928 (19)
O1—C1—O2	121.76 (12)	C9—C10—H10	119.7
O1—C1—C2	129.24 (13)	C11—C10—H10	119.7
O2—C1—C2	109.00 (12)	C12—C11—C10	121.70 (19)
C7—C2—C3	121.84 (12)	C12—C11—H11	119.2
C7—C2—C1	108.45 (11)	C10—C11—H11	119.2
C3—C2—C1	129.69 (14)	C13—C12—C11	117.04 (16)
C4—C3—C2	117.43 (16)	C13—C12—C15	121.9 (2)
C4—C3—H3	121.3	C11—C12—C15	121.0 (2)
C2—C3—H3	121.3	C12—C13—C14	122.56 (18)
C3—C4—C5	120.96 (14)	C12—C13—H13	118.7
C3—C4—H4	119.5	C14—C13—H13	118.7
C5—C4—H4	119.5	C9—C14—C13	119.87 (18)
C4—C5—C6	121.70 (14)	C9—C14—H14	120.1
C4—C5—H5	119.2	C13—C14—H14	120.1
C6—C5—H5	119.2	C16—C15—C12	113.44 (16)
C7—C6—C5	117.46 (16)	C16—C15—H15A	108.9
C7—C6—H6	121.3	C12—C15—H15A	108.9
C5—C6—H6	121.3	C16—C15—H15B	108.9
C2—C7—C6	120.61 (12)	C12—C15—H15B	108.9
C2—C7—C8	109.43 (11)	H15A—C15—H15B	107.7
C6—C7—C8	129.87 (14)	C15—C16—H16A	109.5
N1—C8—C7	114.56 (12)	C15—C16—H16B	109.5
N1—C8—O2	112.79 (12)	H16A—C16—H16B	109.5
C7—C8—O2	102.51 (10)	C15—C16—H16C	109.5
N1—C8—H8	108.9	H16A—C16—H16C	109.5
C7—C8—H8	108.9	H16B—C16—H16C	109.5
O2—C8—H8	108.9	C8—N1—C9	122.24 (13)
C14—C9—C10	118.27 (14)	C8—N1—H1	115.0 (12)
C14—C9—N1	123.11 (15)	C9—N1—H1	114.4 (12)
C10—C9—N1	118.57 (14)	C1—O2—C8	110.56 (10)
C9—C10—C11	120.56 (17)
O1—C1—C2—C7	−179.06 (15)	N1—C9—C10—C11	178.01 (15)
O2—C1—C2—C7	1.31 (16)	C9—C10—C11—C12	−0.2 (3)
O1—C1—C2—C3	2.8 (3)	C10—C11—C12—C13	−0.3 (3)
O2—C1—C2—C3	−176.88 (14)	C10—C11—C12—C15	178.79 (17)
C7—C2—C3—C4	0.3 (2)	C11—C12—C13—C14	0.7 (3)
C1—C2—C3—C4	178.30 (14)	C15—C12—C13—C14	−178.38 (17)
C2—C3—C4—C5	−0.1 (2)	C10—C9—C14—C13	0.0 (2)
C3—C4—C5—C6	0.3 (3)	N1—C9—C14—C13	−177.51 (15)
C4—C5—C6—C7	−0.6 (3)	C12—C13—C14—C9	−0.6 (3)
C3—C2—C7—C6	−0.7 (2)	C13—C12—C15—C16	89.2 (3)
C1—C2—C7—C6	−179.04 (14)	C11—C12—C15—C16	−89.8 (3)
C3—C2—C7—C8	176.26 (13)	C7—C8—N1—C9	172.94 (13)
C1—C2—C7—C8	−2.10 (16)	O2—C8—N1—C9	−70.30 (17)
C5—C6—C7—C2	0.8 (2)	C14—C9—N1—C8	−10.1 (2)
C5—C6—C7—C8	−175.44 (15)	C10—C9—N1—C8	172.45 (14)
C2—C7—C8—N1	124.54 (14)	O1—C1—O2—C8	−179.63 (13)
C6—C7—C8—N1	−58.9 (2)	C2—C1—O2—C8	0.03 (15)
C2—C7—C8—O2	2.02 (15)	N1—C8—O2—C1	−124.93 (13)
C6—C7—C8—O2	178.59 (15)	C7—C8—O2—C1	−1.22 (15)
C14—C9—C10—C11	0.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.928 (19)	2.12 (2)	3.0342 (18)	166.9 (16)
C4—H4···O2^ii	0.93	2.56	3.3574 (17)	144

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