N-(2-Oxo-2H-chromen-3-yl)benzamide.

The phenyl ring in title mol-ecule, C(16)H(11)NO(3), forms a dihedral angle of 7.69 (6)° with the fused ring system. The observed conformation is stabilized by intra-molecular N-H⋯O and C-H⋯O inter-actions. In the crystal, supra-molecular chains are formed along the b axis which are mediated by π-π inter-actions [centroid-centroid distance = 3.614 (2) Å].

Related literature

For the biological activity of imidazoles, see: Yohjiro et al. (1990 ▶). For the anti-inflammatory activity of the title compound, see: Maddi et al. (2007 ▶). Semi-empirical quantum chemical calculations were performed using MOPAC2009 Stewart (2009 ▶).

Experimental

Crystal data

C16H11NO3

M = 265.26

Monoclinic,

a = 12.519 (4) Å

b = 4.748 (3) Å

c = 21.167 (4) Å

β = 102.044 (3)°

V = 1230.5 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.40 × 0.22 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.995

13295 measured reflections

2827 independent reflections

2029 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.11

2827 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008275/hg2654sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008275/hg2654Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H11NO3	F(000) = 552
Mr = 265.26	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3699 reflections
a = 12.519 (4) Å	θ = 2.3–29.6°
b = 4.748 (3) Å	µ = 0.10 mm−1
c = 21.167 (4) Å	T = 293 K
β = 102.044 (3)°	Block, colourless
V = 1230.5 (9) Å3	0.40 × 0.22 × 0.15 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2827 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω and φ scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
Tmin = 0.945, Tmax = 0.995	k = −6→5
13295 measured reflections	l = −27→27

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.2124P] where P = (Fo2 + 2Fc2)/3
2827 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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

	x	y	z	Uiso*/Ueq
O1	0.57658 (10)	0.4385 (3)	0.56046 (6)	0.0705 (4)
O2	0.69047 (9)	0.1338 (2)	0.61603 (5)	0.0526 (3)
O3	0.85472 (10)	0.6200 (3)	0.43753 (6)	0.0667 (4)
N1	0.70508 (10)	0.5787 (3)	0.48003 (6)	0.0443 (3)
H1N	0.6366 (8)	0.619 (4)	0.4767 (8)	0.053*
C1	0.66406 (13)	0.3252 (3)	0.56770 (7)	0.0469 (4)
C2	0.78915 (12)	−0.0059 (3)	0.62787 (7)	0.0426 (3)
C3	0.80701 (14)	−0.1960 (3)	0.67819 (7)	0.0534 (4)
H3	0.7545	−0.2255	0.7027	0.064*
C4	0.90379 (15)	−0.3405 (4)	0.69126 (8)	0.0555 (4)
H4	0.9174	−0.4688	0.7252	0.067*
C5	0.98102 (14)	−0.2972 (4)	0.65453 (8)	0.0552 (4)
H5	1.0463	−0.3974	0.6635	0.066*
C6	0.96208 (13)	−0.1070 (3)	0.60475 (8)	0.0509 (4)
H6	1.0148	−0.0793	0.5802	0.061*
C7	0.86511 (12)	0.0452 (3)	0.59038 (7)	0.0414 (3)
C8	0.84018 (12)	0.2473 (3)	0.53927 (7)	0.0440 (4)
H8	0.8909	0.2863	0.5140	0.053*
C9	0.74390 (12)	0.3800 (3)	0.52784 (6)	0.0403 (3)
C10	0.76069 (13)	0.6840 (3)	0.43656 (7)	0.0440 (4)
C11	0.70075 (12)	0.8878 (3)	0.38827 (7)	0.0408 (3)
C12	0.60296 (13)	1.0138 (3)	0.39149 (7)	0.0500 (4)
H12	0.5684	0.9685	0.4250	0.060*
C13	0.55600 (14)	1.2065 (4)	0.34538 (8)	0.0579 (4)
H13	0.4901	1.2911	0.3481	0.069*
C14	0.60574 (15)	1.2743 (4)	0.29565 (8)	0.0584 (5)
H14	0.5738	1.4047	0.2646	0.070*
C15	0.70244 (15)	1.1497 (4)	0.29178 (8)	0.0590 (5)
H15	0.7360	1.1945	0.2578	0.071*
C16	0.75030 (14)	0.9590 (3)	0.33763 (7)	0.0510 (4)
H16	0.8165	0.8765	0.3348	0.061*

	U11	U22	U33	U12	U13	U23
O1	0.0528 (7)	0.0950 (10)	0.0687 (8)	0.0157 (7)	0.0238 (6)	0.0260 (7)
O2	0.0523 (7)	0.0612 (7)	0.0488 (6)	0.0031 (5)	0.0209 (5)	0.0136 (5)
O3	0.0563 (7)	0.0819 (9)	0.0682 (8)	0.0137 (6)	0.0275 (6)	0.0313 (7)
N1	0.0458 (7)	0.0477 (7)	0.0413 (7)	−0.0018 (6)	0.0135 (6)	0.0049 (5)
C1	0.0461 (9)	0.0543 (9)	0.0415 (8)	−0.0016 (7)	0.0118 (6)	0.0042 (7)
C2	0.0472 (8)	0.0423 (8)	0.0390 (7)	−0.0038 (6)	0.0106 (6)	−0.0016 (6)
C3	0.0634 (10)	0.0557 (9)	0.0434 (8)	−0.0038 (8)	0.0167 (7)	0.0066 (7)
C4	0.0685 (11)	0.0486 (9)	0.0471 (9)	−0.0004 (8)	0.0063 (8)	0.0074 (7)
C5	0.0551 (10)	0.0509 (9)	0.0572 (10)	0.0028 (8)	0.0064 (8)	0.0012 (8)
C6	0.0508 (9)	0.0525 (9)	0.0512 (9)	−0.0005 (7)	0.0149 (7)	−0.0009 (7)
C7	0.0491 (8)	0.0388 (7)	0.0373 (7)	−0.0063 (6)	0.0112 (6)	−0.0043 (6)
C8	0.0504 (9)	0.0449 (8)	0.0401 (7)	−0.0046 (7)	0.0175 (6)	−0.0009 (6)
C9	0.0478 (8)	0.0399 (7)	0.0344 (7)	−0.0063 (6)	0.0115 (6)	−0.0014 (6)
C10	0.0487 (9)	0.0443 (8)	0.0407 (8)	−0.0043 (7)	0.0130 (6)	0.0005 (6)
C11	0.0474 (8)	0.0375 (7)	0.0376 (7)	−0.0066 (6)	0.0090 (6)	−0.0024 (6)
C12	0.0514 (9)	0.0547 (9)	0.0462 (8)	−0.0042 (8)	0.0157 (7)	0.0005 (7)
C13	0.0512 (10)	0.0578 (10)	0.0628 (10)	0.0063 (8)	0.0075 (8)	−0.0003 (8)
C14	0.0706 (12)	0.0501 (9)	0.0506 (9)	0.0028 (8)	0.0037 (8)	0.0078 (8)
C15	0.0740 (12)	0.0572 (10)	0.0485 (9)	0.0024 (9)	0.0191 (8)	0.0113 (8)
C16	0.0570 (9)	0.0527 (9)	0.0463 (8)	0.0035 (8)	0.0177 (7)	0.0036 (7)

O1—C1	1.2009 (19)	C6—H6	0.9300
O2—C1	1.3567 (18)	C7—C8	1.431 (2)
O2—C2	1.3783 (18)	C8—C9	1.336 (2)
O3—C10	1.2118 (18)	C8—H8	0.9300
N1—C10	1.3596 (19)	C10—C11	1.492 (2)
N1—C9	1.3947 (19)	C11—C12	1.377 (2)
N1—H1N	0.867 (9)	C11—C16	1.388 (2)
C1—C9	1.460 (2)	C12—C13	1.377 (2)
C2—C3	1.378 (2)	C12—H12	0.9300
C2—C7	1.381 (2)	C13—C14	1.369 (3)
C3—C4	1.369 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.365 (2)
C4—C5	1.377 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.371 (2)
C5—C6	1.370 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.391 (2)
C1—O2—C2	121.85 (12)	C9—C8—H8	120.0
C10—N1—C9	126.13 (13)	C7—C8—H8	120.0
C10—N1—H1N	120.0 (11)	C8—C9—N1	127.93 (14)
C9—N1—H1N	113.5 (11)	C8—C9—C1	120.79 (13)
O1—C1—O2	117.93 (14)	N1—C9—C1	111.28 (13)
O1—C1—C9	124.25 (14)	O3—C10—N1	121.95 (14)
O2—C1—C9	117.81 (14)	O3—C10—C11	121.49 (13)
O2—C2—C3	116.77 (14)	N1—C10—C11	116.55 (14)
O2—C2—C7	120.63 (13)	C12—C11—C16	118.54 (14)
C3—C2—C7	122.60 (15)	C12—C11—C10	124.99 (14)
C4—C3—C2	118.57 (16)	C16—C11—C10	116.44 (14)
C4—C3—H3	120.7	C11—C12—C13	120.41 (15)
C2—C3—H3	120.7	C11—C12—H12	119.8
C3—C4—C5	120.47 (15)	C13—C12—H12	119.8
C3—C4—H4	119.8	C14—C13—C12	120.40 (17)
C5—C4—H4	119.8	C14—C13—H13	119.8
C6—C5—C4	120.23 (16)	C12—C13—H13	119.8
C6—C5—H5	119.9	C15—C14—C13	119.71 (16)
C4—C5—H5	119.9	C15—C14—H14	120.1
C5—C6—C7	120.90 (15)	C13—C14—H14	120.1
C5—C6—H6	119.5	C14—C15—C16	120.40 (16)
C7—C6—H6	119.5	C14—C15—H15	119.8
C2—C7—C6	117.21 (14)	C16—C15—H15	119.8
C2—C7—C8	118.97 (14)	C15—C16—C11	120.53 (16)
C6—C7—C8	123.82 (14)	C15—C16—H16	119.7
C9—C8—C7	119.94 (14)	C11—C16—H16	119.7
C2—O2—C1—O1	−179.90 (14)	C10—N1—C9—C1	177.37 (14)
C2—O2—C1—C9	0.1 (2)	O1—C1—C9—C8	179.34 (16)
C1—O2—C2—C3	−179.91 (13)	O2—C1—C9—C8	−0.7 (2)
C1—O2—C2—C7	0.0 (2)	O1—C1—C9—N1	−0.5 (2)
O2—C2—C3—C4	179.59 (14)	O2—C1—C9—N1	179.48 (12)
C7—C2—C3—C4	−0.3 (2)	C9—N1—C10—O3	−3.4 (2)
C2—C3—C4—C5	−0.4 (2)	C9—N1—C10—C11	177.89 (13)
C3—C4—C5—C6	0.5 (3)	O3—C10—C11—C12	−166.43 (15)
C4—C5—C6—C7	0.0 (2)	N1—C10—C11—C12	12.3 (2)
O2—C2—C7—C6	−179.11 (13)	O3—C10—C11—C16	11.7 (2)
C3—C2—C7—C6	0.7 (2)	N1—C10—C11—C16	−169.62 (14)
O2—C2—C7—C8	0.5 (2)	C16—C11—C12—C13	−0.2 (2)
C3—C2—C7—C8	−179.65 (14)	C10—C11—C12—C13	177.90 (14)
C5—C6—C7—C2	−0.6 (2)	C11—C12—C13—C14	0.3 (3)
C5—C6—C7—C8	179.82 (14)	C12—C13—C14—C15	0.1 (3)
C2—C7—C8—C9	−1.0 (2)	C13—C14—C15—C16	−0.5 (3)
C6—C7—C8—C9	178.53 (14)	C14—C15—C16—C11	0.6 (3)
C7—C8—C9—N1	−179.05 (13)	C12—C11—C16—C15	−0.3 (2)
C7—C8—C9—C1	1.1 (2)	C10—C11—C16—C15	−178.48 (14)
C10—N1—C9—C8	−2.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.867 (11)	2.236 (16)	2.659 (2)	110.0 (14)
C8—H8···O3	0.93	2.24	2.822 (3)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1	0.87 (1)	2.24 (2)	2.659 (2)	110 (1)
C8—H8⋯O3	0.93	2.24	2.822 (3)	120