Crystal structure of 3-(3,4-di-methyl-anilino)-2-benzo-furan-1(3H)-one.

In the title compound, C16H15NO2, the 2-benzo-furan-1(3H)-one and 3,4-di-methyl-aniline fragments are oriented with a dihedral angle of 89.12 (5)°. N-H⋯O hydrogen-bond inter-actions join mol-ecules into C(6) chains propagating along the a axis. In addition, there are π-π stacking inter-actions between the 2-benzo-furan-one benzene rings [centroid-centroid dis-tance = 3.7870 (13) Å] and C-H⋯π inter-actions between one of the methyl groups and the 3,4-di-methyl-aniline benzene ring.

Related literature

For related crystal structures, see: Li et al. (2009 ▸); Odabaşoğlu & Büyükgüngör (2006a ▸,b ▸, 2007a ▸,b ▸). For graph-set notation, see: Bernstein et al. (1995 ▸).

Experimental

Crystal data

C16H15NO2

M = 253.29

Orthorhombic,

a = 7.3386 (7) Å

b = 14.9133 (11) Å

c = 24.3322 (18) Å

V = 2663.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.38 × 0.23 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.970, T max = 0.988

20839 measured reflections

2906 independent reflections

1660 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.144

S = 1.02

2906 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015009299/gk2634sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009299/gk2634Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009299/gk2634Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009299/gk2634fig1.tif

Mol­ecular structure with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.

Click here for additional data file.

a via PLATON . DOI: 10.1107/S2056989015009299/gk2634fig2.tif

The chains of mol­ecules along the a axis via N—H⋯O hydrogen bond (PLATON; Spek, 2009).

CCDC reference: 1401225

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

C16H15NO2	Dx = 1.264 Mg m−3
Mr = 253.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4689 reflections
a = 7.3386 (7) Å	θ = 1.4–27.0°
b = 14.9133 (11) Å	µ = 0.08 mm−1
c = 24.3322 (18) Å	T = 296 K
V = 2663.0 (4) Å3	Needle, light brown
Z = 8	0.38 × 0.23 × 0.16 mm
F(000) = 1072

Bruker Kappa APEXII CCD diffractometer	2906 independent reflections
Radiation source: fine-focus sealed tube	1660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 7.80 pixels mm-1	θmax = 27.0°, θmin = 2.7°
ω scans	h = −5→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→18
Tmin = 0.970, Tmax = 0.988	l = −31→31
20839 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.3907P] where P = (Fo2 + 2Fc2)/3
2906 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.80336 (19)	0.14473 (8)	0.23068 (5)	0.0528 (4)
O2	0.8396 (2)	0.16231 (9)	0.32129 (5)	0.0614 (4)
N1	0.9466 (2)	0.15132 (10)	0.14175 (6)	0.0533 (5)
H1	1.0572	0.1688	0.1371	0.064*
C1	0.8541 (3)	0.19202 (12)	0.27513 (7)	0.0457 (5)
C2	0.9241 (3)	0.27938 (11)	0.25746 (7)	0.0424 (5)
C3	0.9848 (3)	0.35141 (12)	0.28845 (8)	0.0523 (5)
H3	0.9871	0.3488	0.3266	0.063*
C4	1.0416 (3)	0.42698 (13)	0.26083 (9)	0.0610 (6)
H4	1.0827	0.4765	0.2805	0.073*
C5	1.0381 (3)	0.42990 (13)	0.20393 (10)	0.0651 (6)
H5	1.0775	0.4815	0.1860	0.078*
C6	0.9774 (3)	0.35782 (12)	0.17306 (8)	0.0575 (6)
H6	0.9761	0.3602	0.1349	0.069*
C7	0.9189 (3)	0.28247 (11)	0.20076 (7)	0.0443 (5)
C8	0.8370 (3)	0.19769 (12)	0.17912 (7)	0.0472 (5)
H8	0.7199	0.2115	0.1617	0.057*
C9	0.8834 (3)	0.07697 (11)	0.11132 (7)	0.0463 (5)
C10	1.0086 (3)	0.01250 (12)	0.09499 (7)	0.0521 (5)
H10	1.1299	0.0189	0.1054	0.062*
C11	0.9584 (4)	−0.06119 (12)	0.06359 (7)	0.0572 (6)
C12	0.7769 (4)	−0.07110 (13)	0.04754 (7)	0.0618 (6)
C13	0.6529 (3)	−0.00635 (14)	0.06404 (8)	0.0632 (6)
H13	0.5317	−0.0124	0.0535	0.076*
C14	0.7027 (3)	0.06721 (13)	0.09569 (7)	0.0553 (6)
H14	0.6161	0.1093	0.1063	0.066*
C15	1.1015 (4)	−0.12910 (15)	0.04791 (10)	0.0846 (8)
H15A	1.2147	−0.1140	0.0654	0.127*
H15B	1.1175	−0.1289	0.0087	0.127*
H15C	1.0635	−0.1877	0.0596	0.127*
C16	0.7133 (4)	−0.15104 (15)	0.01424 (10)	0.0953 (9)
H16A	0.5847	−0.1462	0.0076	0.143*
H16B	0.7378	−0.2052	0.0342	0.143*
H16C	0.7769	−0.1524	−0.0202	0.143*

	U11	U22	U33	U12	U13	U23
O1	0.0623 (10)	0.0370 (7)	0.0592 (8)	−0.0047 (6)	0.0027 (7)	−0.0033 (6)
O2	0.0646 (11)	0.0614 (9)	0.0581 (8)	0.0045 (7)	0.0074 (7)	0.0143 (7)
N1	0.0515 (11)	0.0518 (9)	0.0566 (9)	−0.0076 (8)	0.0071 (8)	−0.0179 (7)
C1	0.0457 (12)	0.0391 (10)	0.0524 (11)	0.0075 (9)	0.0045 (9)	0.0000 (9)
C2	0.0434 (12)	0.0356 (9)	0.0481 (10)	0.0067 (9)	−0.0002 (9)	−0.0037 (8)
C3	0.0577 (14)	0.0450 (11)	0.0542 (10)	0.0084 (10)	−0.0029 (10)	−0.0122 (9)
C4	0.0638 (16)	0.0385 (11)	0.0809 (15)	−0.0005 (10)	−0.0047 (12)	−0.0147 (10)
C5	0.0725 (17)	0.0377 (11)	0.0851 (15)	−0.0050 (11)	0.0028 (13)	0.0061 (10)
C6	0.0714 (16)	0.0458 (11)	0.0552 (11)	−0.0007 (11)	0.0001 (11)	0.0060 (9)
C7	0.0481 (12)	0.0355 (9)	0.0493 (10)	0.0038 (9)	−0.0016 (9)	−0.0025 (8)
C8	0.0524 (13)	0.0405 (9)	0.0487 (10)	0.0021 (9)	−0.0026 (9)	−0.0040 (8)
C9	0.0561 (14)	0.0444 (10)	0.0385 (9)	−0.0047 (10)	0.0014 (9)	−0.0042 (8)
C10	0.0591 (14)	0.0495 (11)	0.0476 (10)	0.0010 (11)	0.0013 (10)	−0.0049 (9)
C11	0.0845 (18)	0.0456 (11)	0.0417 (10)	0.0002 (12)	0.0104 (11)	−0.0029 (8)
C12	0.0906 (19)	0.0489 (12)	0.0460 (10)	−0.0145 (13)	0.0064 (12)	−0.0084 (9)
C13	0.0706 (17)	0.0646 (13)	0.0543 (11)	−0.0185 (13)	−0.0032 (11)	−0.0076 (10)
C14	0.0604 (15)	0.0512 (11)	0.0542 (11)	−0.0034 (11)	0.0041 (10)	−0.0084 (9)
C15	0.119 (2)	0.0601 (13)	0.0749 (14)	0.0175 (14)	0.0172 (16)	−0.0143 (12)
C16	0.135 (3)	0.0685 (15)	0.0821 (15)	−0.0301 (16)	0.0022 (17)	−0.0282 (13)

O1—C1	1.344 (2)	C8—H8	0.9800
O1—C8	1.503 (2)	C9—C14	1.387 (3)
O2—C1	1.212 (2)	C9—C10	1.388 (3)
N1—C8	1.397 (2)	C10—C11	1.388 (3)
N1—C9	1.412 (2)	C10—H10	0.9300
N1—H1	0.8600	C11—C12	1.395 (3)
C1—C2	1.465 (3)	C11—C15	1.509 (3)
C2—C7	1.381 (2)	C12—C13	1.386 (3)
C2—C3	1.386 (2)	C12—C16	1.515 (3)
C3—C4	1.377 (3)	C13—C14	1.389 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.385 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.385 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.379 (2)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—C8	1.496 (2)	C16—H16C	0.9600
C1—O1—C8	110.53 (13)	C14—C9—C10	118.79 (17)
C8—N1—C9	122.76 (17)	C14—C9—N1	122.70 (17)
C8—N1—H1	118.6	C10—C9—N1	118.48 (19)
C9—N1—H1	118.6	C9—C10—C11	122.0 (2)
O2—C1—O1	121.98 (17)	C9—C10—H10	119.0
O2—C1—C2	128.89 (17)	C11—C10—H10	119.0
O1—C1—C2	109.12 (15)	C10—C11—C12	119.4 (2)
C7—C2—C3	121.78 (16)	C10—C11—C15	119.1 (2)
C7—C2—C1	108.25 (15)	C12—C11—C15	121.5 (2)
C3—C2—C1	129.96 (17)	C13—C12—C11	118.15 (18)
C4—C3—C2	117.78 (18)	C13—C12—C16	120.0 (2)
C4—C3—H3	121.1	C11—C12—C16	121.8 (2)
C2—C3—H3	121.1	C12—C13—C14	122.5 (2)
C3—C4—C5	120.53 (18)	C12—C13—H13	118.7
C3—C4—H4	119.7	C14—C13—H13	118.7
C5—C4—H4	119.7	C9—C14—C13	119.1 (2)
C6—C5—C4	121.57 (19)	C9—C14—H14	120.4
C6—C5—H5	119.2	C13—C14—H14	120.4
C4—C5—H5	119.2	C11—C15—H15A	109.5
C7—C6—C5	117.87 (18)	C11—C15—H15B	109.5
C7—C6—H6	121.1	H15A—C15—H15B	109.5
C5—C6—H6	121.1	C11—C15—H15C	109.5
C6—C7—C2	120.46 (16)	H15A—C15—H15C	109.5
C6—C7—C8	129.93 (16)	H15B—C15—H15C	109.5
C2—C7—C8	109.55 (15)	C12—C16—H16A	109.5
N1—C8—C7	114.58 (17)	C12—C16—H16B	109.5
N1—C8—O1	112.19 (14)	H16A—C16—H16B	109.5
C7—C8—O1	102.49 (13)	C12—C16—H16C	109.5
N1—C8—H8	109.1	H16A—C16—H16C	109.5
C7—C8—H8	109.1	H16B—C16—H16C	109.5
O1—C8—H8	109.1
C8—O1—C1—O2	−179.85 (17)	C2—C7—C8—N1	−123.94 (17)
C8—O1—C1—C2	0.2 (2)	C6—C7—C8—O1	−179.40 (19)
O2—C1—C2—C7	178.4 (2)	C2—C7—C8—O1	−2.2 (2)
O1—C1—C2—C7	−1.6 (2)	C1—O1—C8—N1	124.55 (17)
O2—C1—C2—C3	−2.8 (4)	C1—O1—C8—C7	1.1 (2)
O1—C1—C2—C3	177.13 (18)	C8—N1—C9—C14	30.1 (3)
C7—C2—C3—C4	−0.4 (3)	C8—N1—C9—C10	−151.93 (17)
C1—C2—C3—C4	−179.03 (19)	C14—C9—C10—C11	0.0 (3)
C2—C3—C4—C5	−0.2 (3)	N1—C9—C10—C11	−178.05 (16)
C3—C4—C5—C6	0.2 (3)	C9—C10—C11—C12	0.3 (3)
C4—C5—C6—C7	0.4 (3)	C9—C10—C11—C15	−179.31 (18)
C5—C6—C7—C2	−1.0 (3)	C10—C11—C12—C13	−0.3 (3)
C5—C6—C7—C8	176.0 (2)	C15—C11—C12—C13	179.33 (18)
C3—C2—C7—C6	1.0 (3)	C10—C11—C12—C16	−178.75 (18)
C1—C2—C7—C6	179.92 (18)	C15—C11—C12—C16	0.9 (3)
C3—C2—C7—C8	−176.51 (17)	C11—C12—C13—C14	0.0 (3)
C1—C2—C7—C8	2.4 (2)	C16—C12—C13—C14	178.46 (19)
C9—N1—C8—C7	−171.10 (16)	C10—C9—C14—C13	−0.3 (3)
C9—N1—C8—O1	72.6 (2)	N1—C9—C14—C13	177.65 (16)
C6—C7—C8—N1	58.8 (3)	C12—C13—C14—C9	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.31	3.025 (2)	141
C15—H15B···Cg3ii	0.96	2.88	3.661 (3)	139

Table 1

Hydrogen-bond geometry (, )

Cg3 is the centroid of the C9C14

DHA	DH	HA	D A	DHA
N1H1O2i	0.86	2.31	3.025(2)	141
C15H15B Cg3ii	0.96	2.88	3.661(3)	139

Symmetry codes: (i) ; (ii) .