7-Diethyl­amino-2-oxo-2H-chromene-3-carboxylic acid

In the title mol­ecular structure, C₁₄H₁₅NO₄, all non-H atoms, except for the C atoms of the terminal methyl groups of the diethyl­amino substituents, are essentially coplanar. In the crystal structure, a two-dimensional network is formed via weak inter­molecular C—H...O hydrogen bonds and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.057
• wR factor = 0.173
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.720     0.997
            Tmin(prime) and Tmax expected:      0.985     0.996
            RR(prime) =      0.730
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.73

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

7-Diethylamino-2-oxo-2H-chromene-3-carboxylic acid

Crystal data

C14H15NO4	F(000) = 552
Mr = 261.27	Dx = 1.402 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9549 reflections
a = 14.1207 (4) Å	θ = 3.0–27.5°
b = 7.7519 (4) Å	µ = 0.10 mm^−1
c = 12.6348 (5) Å	T = 150 K
β = 116.482 (2)°	Plate, orange
V = 1237.92 (9) Å^3	0.14 × 0.12 × 0.04 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	2810 independent reflections
Radiation source: fine-focus sealed tube	1517 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
φ scans and ω scans with κ offsets	h = −18→18
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −10→10
Tmin = 0.720, Tmax = 0.997	l = −16→16
9549 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0876P)^2] where P = (Fo^2 + 2Fc^2)/3
2810 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−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
O1	0.51462 (10)	0.75120 (19)	0.39864 (11)	0.0307 (4)
O2	0.65745 (12)	0.8815 (2)	0.41104 (12)	0.0393 (4)
O3	0.79304 (12)	1.0184 (2)	0.60969 (14)	0.0406 (5)
O4	0.76091 (12)	0.9958 (2)	0.76558 (12)	0.0425 (5)
N1	0.19808 (14)	0.4611 (2)	0.33988 (15)	0.0350 (5)
C1	0.60604 (17)	0.8403 (3)	0.46407 (17)	0.0310 (5)
C2	0.63274 (16)	0.8769 (3)	0.58574 (17)	0.0286 (5)
C3	0.56666 (16)	0.8237 (3)	0.63182 (17)	0.0303 (5)
H3A	0.5850	0.8473	0.7124	0.036*
C4	0.47216 (16)	0.7349 (3)	0.56290 (17)	0.0285 (5)
C5	0.39941 (17)	0.6749 (3)	0.60293 (18)	0.0336 (6)
H5A	0.4133	0.6958	0.6826	0.040*
C6	0.30983 (17)	0.5880 (3)	0.53079 (18)	0.0337 (6)
H6A	0.2623	0.5511	0.5608	0.040*
C7	0.28615 (16)	0.5515 (3)	0.41060 (17)	0.0301 (5)
C8	0.35900 (15)	0.6091 (3)	0.37030 (16)	0.0286 (5)
H8A	0.3465	0.5867	0.2912	0.034*
C9	0.44720 (15)	0.6968 (3)	0.44455 (16)	0.0274 (5)
C10	0.73241 (17)	0.9682 (3)	0.66119 (19)	0.0332 (5)
C11	0.11971 (18)	0.4076 (3)	0.3813 (2)	0.0454 (7)
H11A	0.1576	0.3680	0.4643	0.054*
H11B	0.0786	0.3089	0.3329	0.054*
C12	0.0453 (2)	0.5482 (4)	0.3742 (2)	0.0623 (8)
H12A	−0.0039	0.5059	0.4037	0.093*
H12B	0.0055	0.5852	0.2918	0.093*
H12C	0.0854	0.6461	0.4224	0.093*
C13	0.17047 (18)	0.4311 (3)	0.21478 (18)	0.0365 (6)
H13A	0.1196	0.3342	0.1857	0.044*
H13B	0.2351	0.3961	0.2082	0.044*
C14	0.12251 (19)	0.5863 (3)	0.13588 (19)	0.0467 (7)
H14A	0.1121	0.5601	0.0555	0.070*
H14B	0.1703	0.6853	0.1667	0.070*
H14C	0.0542	0.6140	0.1344	0.070*
H1O	0.757 (2)	0.981 (3)	0.528 (3)	0.073 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0295 (8)	0.0396 (10)	0.0256 (7)	−0.0014 (7)	0.0147 (6)	−0.0007 (6)
O2	0.0386 (9)	0.0511 (11)	0.0336 (8)	−0.0038 (8)	0.0210 (7)	−0.0033 (7)
O3	0.0390 (9)	0.0494 (11)	0.0350 (9)	−0.0061 (8)	0.0182 (8)	−0.0041 (8)
O4	0.0444 (10)	0.0493 (11)	0.0317 (9)	−0.0054 (8)	0.0151 (7)	−0.0071 (7)
N1	0.0324 (10)	0.0434 (12)	0.0329 (10)	−0.0014 (9)	0.0179 (8)	0.0010 (9)
C1	0.0323 (12)	0.0324 (13)	0.0293 (11)	0.0048 (10)	0.0147 (10)	0.0020 (10)
C2	0.0312 (12)	0.0291 (12)	0.0239 (10)	0.0069 (10)	0.0110 (9)	0.0015 (9)
C3	0.0369 (12)	0.0300 (13)	0.0248 (10)	0.0071 (10)	0.0145 (9)	0.0016 (9)
C4	0.0309 (11)	0.0271 (13)	0.0273 (10)	0.0057 (9)	0.0127 (9)	0.0018 (9)
C5	0.0379 (13)	0.0392 (14)	0.0273 (10)	0.0069 (11)	0.0176 (10)	0.0033 (10)
C6	0.0355 (12)	0.0395 (14)	0.0316 (11)	0.0062 (11)	0.0198 (10)	0.0076 (10)
C7	0.0305 (12)	0.0308 (13)	0.0298 (11)	0.0075 (10)	0.0142 (9)	0.0044 (10)
C8	0.0298 (12)	0.0327 (13)	0.0242 (10)	0.0055 (10)	0.0129 (9)	0.0029 (9)
C9	0.0287 (11)	0.0309 (13)	0.0258 (10)	0.0079 (10)	0.0151 (9)	0.0062 (9)
C10	0.0349 (12)	0.0325 (14)	0.0326 (12)	0.0051 (10)	0.0153 (10)	0.0007 (10)
C11	0.0409 (14)	0.0510 (17)	0.0495 (14)	−0.0083 (12)	0.0248 (12)	−0.0060 (12)
C12	0.0477 (16)	0.089 (2)	0.0559 (16)	0.0131 (16)	0.0282 (13)	0.0114 (16)
C13	0.0347 (12)	0.0409 (14)	0.0352 (12)	−0.0041 (11)	0.0168 (10)	−0.0038 (11)
C14	0.0448 (14)	0.0579 (18)	0.0337 (12)	0.0004 (13)	0.0140 (11)	0.0019 (12)

Geometric parameters (Å, º)

O1—C1	1.369 (2)	C6—C7	1.430 (3)
O1—C9	1.383 (2)	C6—H6A	0.9500
O2—C1	1.230 (2)	C7—C8	1.409 (3)
O3—C10	1.343 (3)	C8—C9	1.361 (3)
O3—H1O	0.97 (3)	C8—H8A	0.9500
O4—C10	1.214 (2)	C11—C12	1.488 (3)
N1—C7	1.358 (3)	C11—H11A	0.9900
N1—C13	1.468 (3)	C11—H11B	0.9900
N1—C11	1.479 (3)	C12—H12A	0.9800
C1—C2	1.438 (3)	C12—H12B	0.9800
C2—C3	1.365 (3)	C12—H12C	0.9800
C2—C10	1.481 (3)	C13—C14	1.516 (3)
C3—C4	1.406 (3)	C13—H13A	0.9900
C3—H3A	0.9500	C13—H13B	0.9900
C4—C9	1.406 (3)	C14—H14A	0.9800
C4—C5	1.411 (3)	C14—H14B	0.9800
C5—C6	1.363 (3)	C14—H14C	0.9800
C5—H5A	0.9500
C1—O1—C9	122.71 (15)	C8—C9—C4	123.80 (19)
C10—O3—H1O	106.9 (18)	O1—C9—C4	119.28 (18)
C7—N1—C13	121.05 (18)	O4—C10—O3	120.1 (2)
C7—N1—C11	121.48 (18)	O4—C10—C2	122.9 (2)
C13—N1—C11	117.07 (18)	O3—C10—C2	117.04 (18)
O2—C1—O1	115.39 (17)	N1—C11—C12	113.1 (2)
O2—C1—C2	126.4 (2)	N1—C11—H11A	109.0
O1—C1—C2	118.16 (18)	C12—C11—H11A	109.0
C3—C2—C1	119.53 (19)	N1—C11—H11B	109.0
C3—C2—C10	120.25 (18)	C12—C11—H11B	109.0
C1—C2—C10	120.21 (19)	H11A—C11—H11B	107.8
C2—C3—C4	121.61 (18)	C11—C12—H12A	109.5
C2—C3—H3A	119.2	C11—C12—H12B	109.5
C4—C3—H3A	119.2	H12A—C12—H12B	109.5
C3—C4—C9	118.68 (19)	C11—C12—H12C	109.5
C3—C4—C5	125.52 (19)	H12A—C12—H12C	109.5
C9—C4—C5	115.78 (19)	H12B—C12—H12C	109.5
C6—C5—C4	122.02 (19)	N1—C13—C14	114.13 (19)
C6—C5—H5A	119.0	N1—C13—H13A	108.7
C4—C5—H5A	119.0	C14—C13—H13A	108.7
C5—C6—C7	121.1 (2)	N1—C13—H13B	108.7
C5—C6—H6A	119.5	C14—C13—H13B	108.7
C7—C6—H6A	119.5	H13A—C13—H13B	107.6
N1—C7—C8	121.85 (18)	C13—C14—H14A	109.5
N1—C7—C6	120.84 (19)	C13—C14—H14B	109.5
C8—C7—C6	117.29 (19)	H14A—C14—H14B	109.5
C9—C8—C7	120.05 (18)	C13—C14—H14C	109.5
C9—C8—H8A	120.0	H14A—C14—H14C	109.5
C7—C8—H8A	120.0	H14B—C14—H14C	109.5
C8—C9—O1	116.92 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O···O2	0.97 (3)	1.70 (3)	2.609 (2)	153 (3)
C5—H5A···O1^i	0.95	2.49	3.393 (2)	160
C6—H6A···O4^ii	0.95	2.40	3.228 (3)	146
C13—H13B···O2^iii	0.99	2.57	3.468 (3)	150

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, y−1/2, −z+1/2.