Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound {systematic name: 4-methyl-2-oxo-2H-1-benzopyran-7-yl 3-[4-(dimethyl­amino)phen­yl]prop-2-enoate}, C19H13ClO4, has an E configuration and the dihedral angle between the coumarin unit and the benzene ring is 81.70 (6)°. The mol­ecules are linked by two C—H...O hydrogen bonds into a C(4)C(6)[R21(6)] chain of rings. Adjacent chains are linked by C—H...O hydrogen bonds rings into stepped sheets. Adjacent sheets are linked by weak C—H...O hydrogen bonds into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035586/at2102sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035586/at2102Isup2.hkl
Contains datablock I

CCDC reference: 606729

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.147
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. O1 .. 2.76 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens,1996); cell refinement: SMART; data reduction: SAINT (Siemens,1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4-methyl-2-oxo-2H-1-benzopyran-7-yl 3-[4-(dimethylamino)phenyl]prop-2-enoate top
Crystal data top
C21H19NO4F(000) = 736
Mr = 349.37Dx = 1.306 Mg m3
Monoclinic, P21/cMelting point: 471 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.174 (3) ÅCell parameters from 1461 reflections
b = 9.071 (3) Åθ = 2.5–22.1°
c = 24.175 (9) ŵ = 0.09 mm1
β = 97.670 (6)°T = 298 K
V = 1776.5 (11) Å3Block, yellow
Z = 40.53 × 0.42 × 0.35 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3135 independent reflections
Radiation source: fine-focus sealed tube1480 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 98
Tmin = 0.954, Tmax = 0.969k = 109
9015 measured reflectionsl = 2828
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.0575P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3135 reflectionsΔρmax = 0.17 e Å3
237 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0116 (15)
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.9194 (3)0.2716 (3)0.04477 (11)0.0702 (8)
O10.1772 (2)1.3877 (2)0.24349 (7)0.0558 (6)
O20.0085 (3)1.5044 (2)0.28456 (9)0.0858 (8)
O30.5743 (2)1.1123 (2)0.16305 (7)0.0624 (6)
O40.4815 (3)1.1098 (3)0.07196 (8)0.0891 (8)
C10.0971 (4)1.5174 (3)0.25432 (13)0.0560 (8)
C20.1464 (3)1.6483 (3)0.22918 (11)0.0530 (8)
H20.09201.73550.23550.064*
C30.2669 (4)1.6532 (3)0.19691 (11)0.0490 (8)
C40.3514 (3)1.5180 (3)0.18715 (10)0.0462 (7)
C50.4811 (4)1.5056 (4)0.15472 (12)0.0621 (9)
H50.51901.59000.13870.074*
C60.5532 (4)1.3726 (4)0.14611 (13)0.0675 (9)
H60.63931.36710.12460.081*
C70.4971 (4)1.2479 (4)0.16948 (11)0.0532 (8)
C80.3719 (4)1.2526 (3)0.20194 (10)0.0505 (8)
H80.33521.16740.21780.061*
C90.3024 (3)1.3876 (3)0.21028 (10)0.0452 (7)
C100.3150 (4)1.7942 (3)0.17166 (12)0.0705 (10)
H10A0.23501.86890.17670.106*
H10B0.31911.78000.13250.106*
H10C0.42161.82450.18960.106*
C110.5655 (4)1.0545 (4)0.11046 (12)0.0547 (8)
C120.6634 (3)0.9226 (3)0.11007 (11)0.0535 (8)
H120.73160.89480.14230.064*
C130.6581 (3)0.8394 (3)0.06432 (11)0.0507 (8)
H130.59510.87580.03240.061*
C140.7383 (3)0.7000 (3)0.05862 (11)0.0466 (7)
C150.6928 (3)0.6147 (4)0.01140 (11)0.0541 (8)
H150.61870.65340.01750.065*
C160.7538 (4)0.4744 (4)0.00594 (11)0.0580 (8)
H160.71890.42010.02610.070*
C170.8668 (3)0.4132 (4)0.04770 (11)0.0511 (8)
C180.9203 (3)0.5023 (4)0.09350 (12)0.0595 (9)
H181.00090.46700.12110.071*
C190.8571 (3)0.6409 (4)0.09877 (11)0.0568 (9)
H190.89490.69670.13020.068*
C200.8593 (4)0.1790 (4)0.00179 (13)0.0839 (11)
H20A0.74130.18700.00930.126*
H20B0.88930.07850.00690.126*
H20C0.90710.20980.03410.126*
C211.0429 (4)0.2099 (4)0.08652 (14)0.0951 (13)
H21A1.06370.10940.07710.143*
H21B1.00410.21330.12230.143*
H21C1.14300.26590.08790.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0713 (19)0.058 (2)0.0780 (18)0.0168 (16)0.0037 (15)0.0089 (16)
O10.0674 (13)0.0428 (14)0.0619 (12)0.0021 (11)0.0261 (10)0.0018 (10)
O20.0901 (17)0.0686 (18)0.1117 (18)0.0044 (13)0.0610 (16)0.0062 (14)
O30.0766 (14)0.0628 (16)0.0468 (11)0.0222 (12)0.0042 (10)0.0070 (11)
O40.122 (2)0.0870 (19)0.0527 (13)0.0460 (16)0.0100 (13)0.0082 (13)
C10.063 (2)0.044 (2)0.0631 (19)0.0005 (17)0.0169 (16)0.0073 (16)
C20.0582 (19)0.043 (2)0.0586 (18)0.0041 (16)0.0105 (15)0.0017 (15)
C30.0578 (19)0.041 (2)0.0463 (16)0.0028 (16)0.0009 (14)0.0020 (14)
C40.0506 (18)0.043 (2)0.0454 (16)0.0032 (15)0.0061 (14)0.0007 (14)
C50.070 (2)0.054 (2)0.0665 (19)0.0023 (18)0.0261 (17)0.0037 (16)
C60.061 (2)0.074 (3)0.074 (2)0.003 (2)0.0313 (17)0.0020 (19)
C70.058 (2)0.055 (2)0.0457 (17)0.0115 (18)0.0032 (15)0.0048 (16)
C80.063 (2)0.046 (2)0.0426 (16)0.0019 (16)0.0057 (15)0.0017 (14)
C90.0501 (17)0.048 (2)0.0382 (15)0.0009 (15)0.0075 (13)0.0042 (14)
C100.089 (2)0.050 (2)0.075 (2)0.0028 (19)0.0222 (19)0.0072 (18)
C110.062 (2)0.059 (2)0.0424 (17)0.0099 (17)0.0043 (15)0.0022 (17)
C120.0534 (18)0.058 (2)0.0491 (17)0.0116 (17)0.0065 (14)0.0009 (16)
C130.0507 (18)0.057 (2)0.0447 (16)0.0080 (16)0.0060 (13)0.0040 (15)
C140.0451 (17)0.050 (2)0.0453 (16)0.0054 (15)0.0099 (14)0.0020 (15)
C150.0551 (18)0.059 (2)0.0467 (17)0.0093 (16)0.0003 (14)0.0007 (16)
C160.0578 (19)0.064 (2)0.0512 (17)0.0085 (17)0.0033 (15)0.0087 (16)
C170.0425 (17)0.055 (2)0.0560 (18)0.0054 (16)0.0073 (14)0.0017 (17)
C180.0491 (19)0.063 (2)0.0625 (19)0.0115 (17)0.0055 (15)0.0035 (18)
C190.0513 (19)0.062 (2)0.0556 (18)0.0023 (17)0.0023 (15)0.0088 (16)
C200.090 (3)0.070 (3)0.091 (2)0.020 (2)0.007 (2)0.018 (2)
C210.102 (3)0.080 (3)0.097 (3)0.035 (2)0.014 (2)0.003 (2)
Geometric parameters (Å, º) top
N1—C171.359 (4)C10—H10B0.9600
N1—C201.437 (4)C10—H10C0.9600
N1—C211.442 (4)C11—C121.440 (4)
O1—C91.383 (3)C12—C131.335 (3)
O1—C11.387 (3)C12—H120.9300
O2—C11.209 (3)C13—C141.440 (4)
O3—C111.368 (3)C13—H130.9300
O3—C71.401 (3)C14—C191.386 (4)
O4—C111.191 (3)C14—C151.388 (3)
C1—C21.417 (4)C15—C161.380 (4)
C2—C31.336 (3)C15—H150.9300
C2—H20.9300C16—C171.390 (4)
C3—C41.441 (4)C16—H160.9300
C3—C101.493 (4)C17—C181.394 (4)
C4—C91.390 (4)C18—C191.372 (4)
C4—C51.405 (3)C18—H180.9300
C5—C61.371 (4)C19—H190.9300
C5—H50.9300C20—H20A0.9600
C6—C71.371 (4)C20—H20B0.9600
C6—H60.9300C20—H20C0.9600
C7—C81.371 (4)C21—H21A0.9600
C8—C91.376 (4)C21—H21B0.9600
C8—H80.9300C21—H21C0.9600
C10—H10A0.9600
C17—N1—C20121.0 (3)O4—C11—C12127.4 (3)
C17—N1—C21121.8 (3)O3—C11—C12111.4 (3)
C20—N1—C21117.1 (3)C13—C12—C11121.2 (3)
C9—O1—C1121.0 (2)C13—C12—H12119.4
C11—O3—C7118.1 (2)C11—C12—H12119.4
O2—C1—O1115.1 (3)C12—C13—C14127.7 (3)
O2—C1—C2127.4 (3)C12—C13—H13116.2
O1—C1—C2117.5 (3)C14—C13—H13116.2
C3—C2—C1123.5 (3)C19—C14—C15116.5 (3)
C3—C2—H2118.3C19—C14—C13123.9 (3)
C1—C2—H2118.3C15—C14—C13119.5 (3)
C2—C3—C4118.3 (3)C16—C15—C14122.2 (3)
C2—C3—C10121.4 (3)C16—C15—H15118.9
C4—C3—C10120.3 (3)C14—C15—H15118.9
C9—C4—C5115.8 (3)C15—C16—C17120.9 (3)
C9—C4—C3119.2 (3)C15—C16—H16119.6
C5—C4—C3124.9 (3)C17—C16—H16119.6
C6—C5—C4121.8 (3)N1—C17—C16121.6 (3)
C6—C5—H5119.1N1—C17—C18121.5 (3)
C4—C5—H5119.1C16—C17—C18116.9 (3)
C7—C6—C5119.3 (3)C19—C18—C17121.6 (3)
C7—C6—H6120.3C19—C18—H18119.2
C5—C6—H6120.3C17—C18—H18119.2
C8—C7—C6121.8 (3)C18—C19—C14121.8 (3)
C8—C7—O3118.2 (3)C18—C19—H19119.1
C6—C7—O3119.9 (3)C14—C19—H19119.1
C7—C8—C9117.8 (3)N1—C20—H20A109.5
C7—C8—H8121.1N1—C20—H20B109.5
C9—C8—H8121.1H20A—C20—H20B109.5
C8—C9—O1116.0 (3)N1—C20—H20C109.5
C8—C9—C4123.5 (3)H20A—C20—H20C109.5
O1—C9—C4120.5 (3)H20B—C20—H20C109.5
C3—C10—H10A109.5N1—C21—H21A109.5
C3—C10—H10B109.5N1—C21—H21B109.5
H10A—C10—H10B109.5H21A—C21—H21B109.5
C3—C10—H10C109.5N1—C21—H21C109.5
H10A—C10—H10C109.5H21A—C21—H21C109.5
H10B—C10—H10C109.5H21B—C21—H21C109.5
O4—C11—O3121.2 (3)
C9—O1—C1—O2178.9 (2)C3—C4—C9—C8178.0 (3)
C9—O1—C1—C21.3 (4)C5—C4—C9—O1179.2 (2)
O2—C1—C2—C3178.8 (3)C3—C4—C9—O11.7 (4)
O1—C1—C2—C31.4 (4)C7—O3—C11—O47.3 (4)
C1—C2—C3—C40.0 (4)C7—O3—C11—C12174.6 (3)
C1—C2—C3—C10179.6 (3)O4—C11—C12—C135.5 (5)
C2—C3—C4—C91.5 (4)O3—C11—C12—C13172.5 (3)
C10—C3—C4—C9178.8 (2)C11—C12—C13—C14175.0 (3)
C2—C3—C4—C5179.4 (2)C12—C13—C14—C1910.8 (5)
C10—C3—C4—C50.2 (4)C12—C13—C14—C15166.9 (3)
C9—C4—C5—C60.7 (4)C19—C14—C15—C164.1 (4)
C3—C4—C5—C6178.4 (3)C13—C14—C15—C16173.8 (3)
C4—C5—C6—C70.3 (5)C14—C15—C16—C171.1 (4)
C5—C6—C7—C80.9 (5)C20—N1—C17—C160.2 (4)
C5—C6—C7—O3177.2 (3)C21—N1—C17—C16176.8 (3)
C11—O3—C7—C8118.5 (3)C20—N1—C17—C18177.9 (3)
C11—O3—C7—C665.0 (4)C21—N1—C17—C185.1 (4)
C6—C7—C8—C90.4 (4)C15—C16—C17—N1175.3 (3)
O3—C7—C8—C9176.8 (2)C15—C16—C17—C182.9 (4)
C7—C8—C9—O1179.7 (2)N1—C17—C18—C19174.4 (3)
C7—C8—C9—C40.7 (4)C16—C17—C18—C193.8 (4)
C1—O1—C9—C8179.4 (2)C17—C18—C19—C140.8 (5)
C1—O1—C9—C40.3 (4)C15—C14—C19—C183.2 (4)
C5—C4—C9—C81.2 (4)C13—C14—C19—C18174.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.563.423 (4)154
C10—H10A···O2i0.962.513.426 (4)160
C12—H12···O1ii0.932.763.619 (3)154
C13—H13···O4iii0.932.523.371 (3)152
C15—H15···O4iii0.932.593.402 (4)145
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x+1, y+2, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds