2-Oxochromen-4-yl 4-(dimethyl-amino)-benzoate.

In the title mol-ecule, C(18)H(15)NO(4), the benzoate ring is oriented at a dihedral angle of 43.43 (6)° with respect to the planar [maximum deviation = 0.038 (2) Å] chromene ring. The crystal structure features R(2) (2)(12) centrosymetric dimers formed via C-H⋯O inter-actions and these dimeric aggregates are connected by C-H⋯π inter-actions.

Related literature

For the biological activity of coumarin derivatives, see: Ukhov et al. (2001 ▶); Abd Elhafez et al. (2003 ▶); Basanagouda et al. (2009 ▶); Liu et al. (2008 ▶); Trapkov et al. (1996 ▶); Vukovic et al. (2010 ▶); Emmanuel-Giota et al. (2001 ▶); Hamdi & Dixneuf (2007 ▶); Wang et al. (2001 ▶); Marchenko et al. (2006 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H15NO4

M = 309.32

Triclinic,

a = 7.4939 (2) Å

b = 10.2361 (3) Å

c = 10.6620 (3) Å

α = 92.307 (3)°

β = 103.935 (1)°

γ = 109.852 (2)°

V = 739.92 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.50 × 0.40 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer

8424 measured reflections

3590 independent reflections

2897 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.120

S = 0.98

3585 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030844/tk2767sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030844/tk2767Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030844/tk2767Isup3.cml

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

C18H15NO4	Z = 2
Mr = 309.32	F(000) = 324
Triclinic, P1	Dx = 1.388 Mg m−3
Hall symbol: -P 1	Melting point: 445 K
a = 7.4939 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2361 (3) Å	Cell parameters from 8424 reflections
c = 10.6620 (3) Å	θ = 2.0–28.7°
α = 92.307 (3)°	µ = 0.10 mm−1
β = 103.935 (1)°	T = 298 K
γ = 109.852 (2)°	Parallelepiped, colourless
V = 739.92 (4) Å3	0.50 × 0.40 × 0.30 mm

Nonius KappaCCD diffractometer	2897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 28.7°, θmin = 2.0°
φ and ω scans	h = −9→9
8424 measured reflections	k = −13→13
3590 independent reflections	l = −14→14

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) = 0.120	H-atom parameters constrained
S = 0.98	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.05P)2 + 0.22P], where P = [max(Fo2,0) + 2Fc2]/3
3585 reflections	(Δ/σ)max = 0.00023
208 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3
60 constraints

Refinement. The 5 reflections 1 0 0; 0 1 0; -1 0 1; 0 0 1; -1 1 1 have been measured with too low intensities. It might be caused by some systematical error, probably by shielding by a beam stop of these diffractions. They were not used in the refinement.

	x	y	z	Uiso*/Ueq
O1	0.16941 (15)	0.34698 (9)	−0.00111 (8)	0.0462
C2	0.13553 (19)	0.27238 (13)	−0.11979 (11)	0.0385
C3	0.16678 (17)	0.14123 (12)	−0.10953 (12)	0.0363
C4	0.12326 (18)	0.05485 (13)	−0.22545 (12)	0.0396
O5	0.05704 (15)	0.09384 (10)	−0.34457 (9)	0.0493
C6	0.0349 (2)	0.22168 (15)	−0.35487 (13)	0.0480
C7	0.0715 (2)	0.31027 (14)	−0.23575 (13)	0.0453
O8	−0.0149 (2)	0.24941 (13)	−0.46358 (10)	0.0703
C9	0.1466 (2)	−0.07411 (14)	−0.22593 (15)	0.0499
C10	0.2154 (2)	−0.11591 (15)	−0.10867 (16)	0.0531
C11	0.2611 (2)	−0.03116 (15)	0.00810 (15)	0.0504
C12	0.2373 (2)	0.09635 (14)	0.00783 (13)	0.0436
C13	0.26101 (19)	0.49181 (13)	0.02252 (12)	0.0394
O14	0.31022 (19)	0.56038 (11)	−0.06000 (10)	0.0605
C15	0.29273 (18)	0.54219 (12)	0.15893 (11)	0.0361
C16	0.40333 (19)	0.68335 (13)	0.20353 (12)	0.0399
C17	0.4486 (2)	0.73643 (14)	0.33261 (13)	0.0438
C18	0.38190 (19)	0.64988 (14)	0.42412 (12)	0.0399
N19	0.42952 (19)	0.70056 (13)	0.55279 (11)	0.0513
C20	0.3356 (3)	0.61733 (19)	0.64173 (14)	0.0591
C21	0.5486 (4)	0.8446 (2)	0.59983 (17)	0.0903
C22	0.2647 (2)	0.50796 (14)	0.37750 (12)	0.0422
C23	0.22417 (19)	0.45612 (13)	0.24879 (12)	0.0402
H71	0.0500	0.3963	−0.2441	0.0557*
H91	0.1132	−0.1320	−0.3079	0.0600*
H101	0.2329	−0.2053	−0.1062	0.0641*
H111	0.3097	−0.0605	0.0902	0.0601*
H121	0.2673	0.1552	0.0875	0.0528*
H161	0.4492	0.7442	0.1416	0.0485*
H171	0.5265	0.8322	0.3594	0.0528*
H201	0.3856	0.6702	0.7280	0.0885*
H203	0.1930	0.5921	0.6121	0.0885*
H202	0.3622	0.5286	0.6450	0.0885*
H211	0.5837	0.8563	0.6932	0.1350*
H213	0.4752	0.9046	0.5672	0.1350*
H212	0.6655	0.8711	0.5708	0.1350*
H221	0.2121	0.4466	0.4367	0.0519*
H231	0.1484	0.3589	0.2193	0.0481*

	U11	U22	U33	U12	U13	U23
O1	0.0692 (6)	0.0362 (5)	0.0336 (4)	0.0168 (4)	0.0184 (4)	0.0015 (4)
C2	0.0442 (7)	0.0376 (6)	0.0332 (6)	0.0136 (5)	0.0122 (5)	0.0005 (5)
C3	0.0355 (6)	0.0348 (6)	0.0363 (6)	0.0096 (5)	0.0109 (5)	0.0019 (5)
C4	0.0397 (6)	0.0371 (6)	0.0375 (6)	0.0095 (5)	0.0095 (5)	0.0001 (5)
O5	0.0631 (6)	0.0452 (5)	0.0345 (5)	0.0183 (5)	0.0072 (4)	−0.0028 (4)
C6	0.0555 (8)	0.0498 (8)	0.0358 (6)	0.0196 (6)	0.0069 (6)	0.0016 (6)
C7	0.0571 (8)	0.0444 (7)	0.0378 (6)	0.0241 (6)	0.0105 (6)	0.0042 (5)
O8	0.1030 (10)	0.0720 (8)	0.0340 (5)	0.0396 (7)	0.0038 (5)	0.0047 (5)
C9	0.0537 (8)	0.0389 (7)	0.0534 (8)	0.0137 (6)	0.0140 (6)	−0.0039 (6)
C10	0.0543 (8)	0.0396 (7)	0.0668 (9)	0.0197 (6)	0.0150 (7)	0.0058 (6)
C11	0.0500 (8)	0.0478 (8)	0.0534 (8)	0.0194 (6)	0.0104 (6)	0.0122 (6)
C12	0.0467 (7)	0.0439 (7)	0.0382 (6)	0.0149 (6)	0.0099 (5)	0.0052 (5)
C13	0.0487 (7)	0.0361 (6)	0.0357 (6)	0.0171 (5)	0.0133 (5)	0.0045 (5)
O14	0.0936 (8)	0.0462 (6)	0.0392 (5)	0.0159 (5)	0.0266 (5)	0.0087 (4)
C15	0.0419 (6)	0.0361 (6)	0.0331 (6)	0.0161 (5)	0.0124 (5)	0.0044 (5)
C16	0.0461 (7)	0.0368 (6)	0.0379 (6)	0.0129 (5)	0.0159 (5)	0.0076 (5)
C17	0.0477 (7)	0.0367 (6)	0.0415 (7)	0.0090 (5)	0.0120 (5)	0.0012 (5)
C18	0.0423 (7)	0.0456 (7)	0.0324 (6)	0.0185 (5)	0.0077 (5)	0.0033 (5)
N19	0.0632 (8)	0.0545 (7)	0.0319 (5)	0.0193 (6)	0.0086 (5)	0.0011 (5)
C20	0.0716 (10)	0.0777 (11)	0.0347 (7)	0.0325 (9)	0.0179 (7)	0.0104 (7)
C21	0.1312 (19)	0.0643 (11)	0.0409 (9)	0.0037 (11)	0.0096 (10)	−0.0089 (8)
C22	0.0506 (7)	0.0418 (7)	0.0366 (6)	0.0160 (6)	0.0163 (5)	0.0102 (5)
C23	0.0474 (7)	0.0344 (6)	0.0385 (6)	0.0128 (5)	0.0139 (5)	0.0048 (5)

O1—C2	1.3728 (14)	C13—C15	1.4586 (16)
O1—C13	1.3885 (15)	C15—C16	1.3937 (17)
C2—C3	1.4430 (17)	C15—C23	1.3985 (17)
C2—C7	1.3373 (18)	C16—C17	1.3762 (17)
C3—C4	1.3920 (16)	C16—H161	0.969
C3—C12	1.3958 (17)	C17—C18	1.4110 (18)
C4—O5	1.3749 (15)	C17—H171	0.944
C4—C9	1.3892 (18)	C18—N19	1.3637 (16)
O5—C6	1.3794 (17)	C18—C22	1.4121 (18)
C6—C7	1.4425 (18)	N19—C20	1.4490 (19)
C6—O8	1.2056 (16)	N19—C21	1.433 (2)
C7—H71	0.952	C20—H201	0.967
C9—C10	1.376 (2)	C20—H203	0.976
C9—H91	0.965	C20—H202	0.994
C10—C11	1.388 (2)	C21—H211	0.958
C10—H101	0.967	C21—H213	0.977
C11—C12	1.3764 (19)	C21—H212	0.956
C11—H111	0.965	C22—C23	1.3742 (17)
C12—H121	0.954	C22—H221	0.965
C13—O14	1.1970 (15)	C23—H231	0.958
C2—O1—C13	122.05 (10)	C13—C15—C23	123.81 (11)
O1—C2—C3	113.36 (10)	C16—C15—C23	117.98 (11)
O1—C2—C7	125.23 (12)	C15—C16—C17	121.34 (11)
C3—C2—C7	121.35 (11)	C15—C16—H161	118.6
C2—C3—C4	117.02 (11)	C17—C16—H161	120.1
C2—C3—C12	124.46 (11)	C16—C17—C18	120.99 (12)
C4—C3—C12	118.52 (12)	C16—C17—H171	118.8
C3—C4—O5	121.54 (11)	C18—C17—H171	120.2
C3—C4—C9	121.44 (12)	C17—C18—N19	121.52 (12)
O5—C4—C9	117.02 (11)	C17—C18—C22	117.38 (11)
C4—O5—C6	121.54 (10)	N19—C18—C22	121.10 (12)
O5—C6—C7	117.73 (11)	C18—N19—C20	120.85 (12)
O5—C6—O8	116.75 (12)	C18—N19—C21	120.98 (13)
C7—C6—O8	125.52 (14)	C20—N19—C21	117.41 (13)
C6—C7—C2	120.70 (12)	N19—C20—H201	109.4
C6—C7—H71	116.9	N19—C20—H203	110.3
C2—C7—H71	122.4	H201—C20—H203	109.8
C4—C9—C10	118.74 (13)	N19—C20—H202	110.5
C4—C9—H91	119.3	H201—C20—H202	109.5
C10—C9—H91	121.9	H203—C20—H202	107.3
C9—C10—C11	120.87 (13)	N19—C21—H211	108.5
C9—C10—H101	120.4	N19—C21—H213	110.0
C11—C10—H101	118.7	H211—C21—H213	109.9
C10—C11—C12	120.06 (13)	N19—C21—H212	110.5
C10—C11—H111	120.8	H211—C21—H212	109.4
C12—C11—H111	119.2	H213—C21—H212	108.5
C3—C12—C11	120.37 (12)	C18—C22—C23	120.82 (12)
C3—C12—H121	118.8	C18—C22—H221	119.6
C11—C12—H121	120.8	C23—C22—H221	119.6
O1—C13—O14	122.43 (11)	C15—C23—C22	121.45 (12)
O1—C13—C15	110.44 (10)	C15—C23—H231	118.7
O14—C13—C15	127.08 (12)	C22—C23—H231	119.9
C13—C15—C16	118.18 (11)

Cg3 is the centroid of the benzoate-benzene ring (C15–C18/C22/C23).

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···O8i	0.96	2.49	3.449 (2)	171
C7—H71···Cg3ii	0.95	2.84	3.429 (2)	121
C20—H202···Cg3iii	0.99	2.91	3.777 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C18/C22/C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H91⋯O8i	0.96	2.49	3.449 (2)	171
C7—H71⋯Cg3ii	0.95	2.84	3.429 (2)	121
C20—H202⋯Cg3iii	0.99	2.91	3.777 (2)	146

Symmetry codes: (i) ; (ii) ; (iii) .