supplementary materials


cv5061 scheme

Acta Cryst. (2011). E67, o1107    [ doi:10.1107/S1600536811010944 ]

7-Diethylamino-2-oxo-2H-chromene-3-carbohydrazide

L.-J. Zhang and B.-Z. Yin

Abstract top

The asymmetric unit of the title compound, C14H17N3O3, contains two independent molecules with different conformations of the ethyl groups. In the crystal, intermolecular N-H...O hydrogen bonds link the molecules into ribbons extending along the a axis.

Comment top

Coumarin derivatives have received considerable attention since their diverse bioactivities and chemiluminescence (Munasinghe et al. 2007). Herein, we report the crystal structure of the title compound, an important organic intermediate and a fluorescent tagging agent for chemosensors.

In the title compound, all bond lengths and angles are normal and comparable to those observed in the related struture (Yu et al., 2009). There are two independent molecules in the asymmetric unit with different conformation of the ethyl groups (Fig. 1). Except for four terminal carbon atoms, the other non-hydrogen atoms are nearly coplanar for two components [mean deviations from the mean planes are 0.065 (1) and 0.07 (1), respectively] and form an angle of 19.39 (4) °. Intermolecuar N—H···O hydrogen bonds (Table 1) link the molecules into ribbons extended along axis a.

Related literature top

For the bioactivity and chemiluminescence of coumarin derivatives, see: Munasinghe et al. (2007). For a related structure, see: Yu et al. (2009). For details of the synthesis, see: Ma et al. (2010).

Experimental top

The title compound was prepared according to the literature (Ma et al., 2010). Single crystals suitable for X-ray diffraction were prepared by slow evaporation a mixture of dichloromethane and petroleum (60–90 °C) at room temperature.

Refinement top

C-bound H-atoms were placed in calculated positions with C—H = 0.93, 096 or 0.97 Å and were included in the refinement in the riding model with Uiso(H) = 1.2 or 1.5 Ueq(C). The H of nitrogen atom were located from differecne Fourier Map and refined with N—H bond lengths restrained to 0.87 (3) Å, and with Uiso(H) = 1.5 Ueq(N).

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Two independent molecules of the title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level.
7-Diethylamino-2-oxo-2H-chromene-3-carbohydrazide top
Crystal data top
C14H17N3O3Z = 4
Mr = 275.31F(000) = 584
Triclinic, P1Dx = 1.338 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3438 (19) ÅCell parameters from 8202 reflections
b = 12.771 (3) Åθ = 3.2–27.5°
c = 12.978 (3) ŵ = 0.10 mm1
α = 95.17 (3)°T = 290 K
β = 110.13 (3)°Block, yellow
γ = 106.18 (3)°0.14 × 0.12 × 0.11 mm
V = 1366.4 (5) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6186 independent reflections
Radiation source: fine-focus sealed tube3402 reflections with I > 2σ(I)
graphiteRint = 0.030
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1210
Tmin = 0.987, Tmax = 0.990k = 1616
13506 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0543P)2]
where P = (Fo2 + 2Fc2)/3
6186 reflections(Δ/σ)max = 0.005
383 parametersΔρmax = 0.18 e Å3
6 restraintsΔρmin = 0.19 e Å3
Crystal data top
C14H17N3O3γ = 106.18 (3)°
Mr = 275.31V = 1366.4 (5) Å3
Triclinic, P1Z = 4
a = 9.3438 (19) ÅMo Kα radiation
b = 12.771 (3) ŵ = 0.10 mm1
c = 12.978 (3) ÅT = 290 K
α = 95.17 (3)°0.14 × 0.12 × 0.11 mm
β = 110.13 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6186 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3402 reflections with I > 2σ(I)
Tmin = 0.987, Tmax = 0.990Rint = 0.030
13506 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117Δρmax = 0.18 e Å3
S = 1.01Δρmin = 0.19 e Å3
6186 reflectionsAbsolute structure: ?
383 parametersFlack parameter: ?
6 restraintsRogers parameter: ?
Special details top

Experimental. (See detailed section in the paper)

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
C10.21139 (18)0.57501 (13)1.19989 (14)0.0463 (4)
C20.13466 (18)0.48762 (12)1.24574 (13)0.0436 (4)
C30.13127 (19)0.50961 (13)1.35921 (14)0.0492 (4)
C40.06725 (18)0.38172 (12)1.18533 (13)0.0463 (4)
H40.01500.32651.21460.056*
C50.07300 (18)0.35191 (12)1.08046 (13)0.0443 (4)
C60.15295 (17)0.43610 (12)1.03866 (13)0.0426 (4)
C70.17389 (18)0.41745 (13)0.93993 (14)0.0494 (4)
H70.22890.47640.91590.059*
C80.11153 (18)0.30841 (13)0.87521 (13)0.0484 (4)
C90.02840 (19)0.22172 (13)0.91645 (14)0.0524 (4)
H90.01440.14890.87540.063*
C100.01086 (19)0.24390 (13)1.01450 (14)0.0516 (4)
H100.04430.18551.03910.062*
C110.0769 (2)0.17291 (15)0.71424 (16)0.0645 (5)
H11A0.09600.12390.76660.077*
H11B0.14110.16990.66980.077*
C120.0988 (2)0.13259 (17)0.63824 (16)0.0768 (6)
H12A0.16250.13750.68170.115*
H12B0.12950.05650.60130.115*
H12C0.11680.17800.58320.115*
C130.2090 (2)0.37670 (15)0.72996 (15)0.0640 (5)
H13A0.18280.44300.74620.077*
H13B0.16870.35320.64910.077*
C140.3890 (2)0.40375 (17)0.77862 (19)0.0777 (6)
H14A0.43010.43330.85770.116*
H14B0.43710.45800.74300.116*
H14C0.41490.33730.76620.116*
C150.2466 (2)0.11381 (14)1.16812 (14)0.0526 (4)
C160.36577 (19)0.22392 (14)1.21170 (14)0.0506 (4)
C170.3901 (2)0.29587 (15)1.31736 (15)0.0556 (4)
C180.4607 (2)0.26342 (14)1.15444 (14)0.0544 (4)
H180.53590.33491.18190.065*
C190.44932 (19)0.20030 (13)1.05563 (14)0.0493 (4)
C200.33527 (18)0.09381 (13)1.01525 (13)0.0466 (4)
C210.31367 (19)0.02453 (13)0.92049 (14)0.0512 (4)
H210.23450.04540.89620.061*
C220.41151 (19)0.05924 (13)0.85967 (14)0.0494 (4)
C230.5282 (2)0.16798 (14)0.90010 (14)0.0547 (4)
H230.59360.19390.86140.066*
C240.5454 (2)0.23412 (14)0.99384 (15)0.0571 (4)
H240.62360.30451.01840.069*
C250.4975 (2)0.02687 (16)0.70252 (16)0.0687 (5)
H25A0.50550.03860.66390.082*
H25B0.60540.07170.75470.082*
C260.4354 (3)0.09271 (17)0.61840 (16)0.0806 (6)
H26A0.32850.04900.56630.121*
H26B0.50550.11170.57860.121*
H26C0.43220.15960.65630.121*
C270.2699 (2)0.11834 (14)0.72177 (16)0.0646 (5)
H27A0.26790.15510.78370.078*
H27B0.29890.16270.67270.078*
C280.1023 (2)0.11651 (16)0.65768 (16)0.0717 (5)
H28A0.06640.08110.70770.108*
H28B0.02990.19150.62530.108*
H28C0.10400.07580.59920.108*
N10.12851 (17)0.28688 (11)0.77682 (12)0.0596 (4)
N20.19388 (19)0.61432 (12)1.41508 (12)0.0581 (4)
H20.231 (2)0.6657 (13)1.3829 (16)0.087*
N30.1989 (2)0.64809 (13)1.52280 (14)0.0672 (4)
H3B0.268 (2)0.6211 (18)1.5658 (15)0.101*
H3A0.1032 (15)0.6189 (17)1.5226 (19)0.101*
N40.39535 (17)0.00890 (12)0.76634 (12)0.0579 (4)
N50.3063 (2)0.25209 (14)1.37695 (14)0.0663 (4)
H50.241 (2)0.1841 (10)1.3507 (18)0.099*
N60.3254 (2)0.30988 (17)1.48147 (15)0.0782 (5)
H6B0.270 (3)0.3544 (18)1.470 (2)0.117*
H6A0.4263 (14)0.3504 (18)1.5136 (19)0.117*
O10.21779 (13)0.54484 (8)1.09751 (9)0.0493 (3)
O20.27280 (15)0.67378 (9)1.24139 (10)0.0638 (3)
O30.07200 (17)0.43205 (10)1.39865 (11)0.0697 (4)
O40.23680 (13)0.05352 (9)1.07136 (9)0.0542 (3)
O50.15179 (15)0.06693 (10)1.20795 (11)0.0694 (4)
O60.48723 (17)0.39132 (11)1.34921 (11)0.0751 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0444 (9)0.0409 (9)0.0559 (10)0.0098 (7)0.0261 (8)0.0083 (8)
C20.0416 (8)0.0405 (8)0.0540 (10)0.0136 (7)0.0244 (8)0.0110 (7)
C30.0499 (9)0.0471 (9)0.0602 (11)0.0185 (8)0.0302 (8)0.0131 (8)
C40.0442 (9)0.0412 (9)0.0556 (10)0.0098 (7)0.0238 (8)0.0152 (8)
C50.0424 (8)0.0398 (8)0.0497 (9)0.0092 (7)0.0195 (7)0.0114 (7)
C60.0362 (8)0.0362 (8)0.0508 (10)0.0065 (7)0.0163 (7)0.0063 (7)
C70.0488 (9)0.0415 (9)0.0561 (10)0.0046 (7)0.0268 (8)0.0080 (8)
C80.0442 (9)0.0478 (9)0.0495 (10)0.0091 (8)0.0199 (8)0.0051 (8)
C90.0530 (10)0.0374 (8)0.0553 (11)0.0043 (8)0.0177 (8)0.0028 (8)
C100.0530 (10)0.0392 (8)0.0568 (11)0.0031 (8)0.0236 (8)0.0107 (8)
C110.0749 (13)0.0558 (11)0.0622 (12)0.0167 (10)0.0326 (10)0.0004 (9)
C120.0884 (15)0.0648 (12)0.0565 (12)0.0097 (11)0.0179 (11)0.0050 (10)
C130.0696 (12)0.0645 (12)0.0595 (12)0.0189 (10)0.0313 (10)0.0050 (9)
C140.0777 (14)0.0684 (13)0.1055 (17)0.0265 (11)0.0537 (13)0.0260 (12)
C150.0563 (10)0.0527 (10)0.0567 (11)0.0170 (9)0.0300 (9)0.0196 (9)
C160.0521 (10)0.0534 (10)0.0534 (10)0.0198 (8)0.0252 (8)0.0191 (8)
C170.0559 (10)0.0583 (11)0.0579 (11)0.0219 (10)0.0240 (9)0.0202 (9)
C180.0549 (10)0.0469 (9)0.0607 (11)0.0109 (8)0.0250 (9)0.0161 (9)
C190.0505 (9)0.0470 (9)0.0515 (10)0.0100 (8)0.0245 (8)0.0168 (8)
C200.0456 (9)0.0469 (9)0.0530 (10)0.0114 (8)0.0265 (8)0.0208 (8)
C210.0521 (10)0.0441 (9)0.0586 (11)0.0078 (8)0.0276 (9)0.0168 (8)
C220.0505 (9)0.0503 (9)0.0535 (10)0.0155 (8)0.0261 (8)0.0192 (8)
C230.0531 (10)0.0576 (10)0.0560 (11)0.0089 (8)0.0296 (9)0.0208 (9)
C240.0576 (10)0.0482 (10)0.0611 (11)0.0010 (8)0.0297 (9)0.0161 (9)
C250.0768 (13)0.0694 (12)0.0750 (13)0.0238 (11)0.0470 (11)0.0165 (11)
C260.0798 (14)0.0811 (14)0.0630 (13)0.0053 (12)0.0223 (11)0.0185 (11)
C270.0742 (13)0.0515 (10)0.0740 (13)0.0163 (10)0.0409 (11)0.0064 (9)
C280.0660 (12)0.0690 (12)0.0765 (14)0.0100 (10)0.0366 (11)0.0004 (10)
N10.0636 (9)0.0501 (8)0.0602 (9)0.0039 (7)0.0324 (8)0.0005 (7)
N20.0738 (10)0.0494 (9)0.0568 (10)0.0158 (8)0.0362 (8)0.0081 (7)
N30.0833 (12)0.0614 (10)0.0638 (11)0.0183 (9)0.0431 (10)0.0042 (8)
N40.0605 (9)0.0560 (9)0.0631 (10)0.0128 (7)0.0359 (8)0.0124 (8)
N50.0763 (11)0.0713 (10)0.0619 (10)0.0225 (9)0.0404 (9)0.0155 (9)
N60.0926 (13)0.0951 (14)0.0573 (11)0.0356 (11)0.0380 (10)0.0145 (10)
O10.0545 (6)0.0380 (6)0.0568 (7)0.0050 (5)0.0322 (6)0.0062 (5)
O20.0802 (8)0.0391 (6)0.0750 (8)0.0036 (6)0.0481 (7)0.0033 (6)
O30.0996 (10)0.0517 (7)0.0758 (9)0.0195 (7)0.0587 (8)0.0168 (7)
O40.0581 (7)0.0490 (6)0.0606 (7)0.0078 (5)0.0360 (6)0.0146 (6)
O50.0763 (9)0.0634 (8)0.0779 (9)0.0078 (7)0.0526 (8)0.0166 (7)
O60.0871 (10)0.0642 (9)0.0697 (9)0.0104 (8)0.0380 (8)0.0079 (7)
Geometric parameters (Å, °) top
C1—O21.2131 (19)C16—C171.489 (2)
C1—O11.3757 (18)C17—O61.231 (2)
C1—C21.443 (2)C17—N51.332 (2)
C2—C41.354 (2)C18—C191.406 (2)
C2—C31.487 (2)C18—H180.9300
C3—O31.2372 (19)C19—C201.393 (2)
C3—N21.324 (2)C19—C241.406 (2)
C4—C51.403 (2)C20—C211.367 (2)
C4—H40.9300C20—O41.3808 (17)
C5—C61.395 (2)C21—C221.410 (2)
C5—C101.404 (2)C21—H210.9300
C6—C71.371 (2)C22—N41.363 (2)
C6—O11.3785 (18)C22—C231.422 (2)
C7—C81.409 (2)C23—C241.350 (2)
C7—H70.9300C23—H230.9300
C8—N11.3534 (19)C24—H240.9300
C8—C91.425 (2)C25—N41.475 (2)
C9—C101.353 (2)C25—C261.496 (3)
C9—H90.9300C25—H25A0.9700
C10—H100.9300C25—H25B0.9700
C11—N11.462 (2)C26—H26A0.9600
C11—C121.502 (3)C26—H26B0.9600
C11—H11A0.9700C26—H26C0.9600
C11—H11B0.9700C27—N41.462 (2)
C12—H12A0.9600C27—C281.507 (3)
C12—H12B0.9600C27—H27A0.9700
C12—H12C0.9600C27—H27B0.9700
C13—N11.487 (2)C28—H28A0.9600
C13—C141.501 (3)C28—H28B0.9600
C13—H13A0.9700C28—H28C0.9600
C13—H13B0.9700N2—N31.406 (2)
C14—H14A0.9600N2—H20.86 (3)
C14—H14B0.9600N3—H3B0.87 (3)
C14—H14C0.9600N3—H3A0.87 (3)
C15—O51.2187 (18)N5—N61.413 (2)
C15—O41.3732 (19)N5—H50.87 (3)
C15—C161.445 (3)N6—H6B0.86 (3)
C16—C181.366 (2)N6—H6A0.87 (3)
O2—C1—O1115.01 (14)C16—C18—H18118.7
O2—C1—C2127.53 (15)C19—C18—H18118.7
O1—C1—C2117.45 (14)C20—C19—C18117.92 (15)
C4—C2—C1119.34 (14)C20—C19—C24116.24 (16)
C4—C2—C3118.69 (14)C18—C19—C24125.83 (16)
C1—C2—C3121.94 (14)C21—C20—O4116.70 (14)
O3—C3—N2122.13 (15)C21—C20—C19123.23 (14)
O3—C3—C2120.46 (15)O4—C20—C19120.07 (14)
N2—C3—C2117.41 (14)C20—C21—C22119.95 (16)
C2—C4—C5122.75 (14)C20—C21—H21120.0
C2—C4—H4118.6C22—C21—H21120.0
C5—C4—H4118.6N4—C22—C21121.31 (16)
C6—C5—C4117.57 (14)N4—C22—C23121.43 (15)
C6—C5—C10116.19 (14)C21—C22—C23117.25 (16)
C4—C5—C10126.19 (14)C24—C23—C22121.02 (15)
C7—C6—O1116.17 (13)C24—C23—H23119.5
C7—C6—C5123.47 (14)C22—C23—H23119.5
O1—C6—C5120.35 (13)C23—C24—C19122.30 (16)
C6—C7—C8119.52 (15)C23—C24—H24118.9
C6—C7—H7120.2C19—C24—H24118.9
C8—C7—H7120.2N4—C25—C26113.65 (15)
N1—C8—C7121.23 (15)N4—C25—H25A108.8
N1—C8—C9121.16 (15)C26—C25—H25A108.8
C7—C8—C9117.60 (14)N4—C25—H25B108.8
C10—C9—C8120.88 (15)C26—C25—H25B108.8
C10—C9—H9119.6H25A—C25—H25B107.7
C8—C9—H9119.6C25—C26—H26A109.5
C9—C10—C5122.33 (15)C25—C26—H26B109.5
C9—C10—H10118.8H26A—C26—H26B109.5
C5—C10—H10118.8C25—C26—H26C109.5
N1—C11—C12111.83 (15)H26A—C26—H26C109.5
N1—C11—H11A109.3H26B—C26—H26C109.5
C12—C11—H11A109.3N4—C27—C28114.99 (15)
N1—C11—H11B109.3N4—C27—H27A108.5
C12—C11—H11B109.3C28—C27—H27A108.5
H11A—C11—H11B107.9N4—C27—H27B108.5
C11—C12—H12A109.5C28—C27—H27B108.5
C11—C12—H12B109.5H27A—C27—H27B107.5
H12A—C12—H12B109.5C27—C28—H28A109.5
C11—C12—H12C109.5C27—C28—H28B109.5
H12A—C12—H12C109.5H28A—C28—H28B109.5
H12B—C12—H12C109.5C27—C28—H28C109.5
N1—C13—C14111.26 (15)H28A—C28—H28C109.5
N1—C13—H13A109.4H28B—C28—H28C109.5
C14—C13—H13A109.4C8—N1—C11121.48 (14)
N1—C13—H13B109.4C8—N1—C13122.05 (14)
C14—C13—H13B109.4C11—N1—C13116.37 (13)
H13A—C13—H13B108.0C3—N2—N3123.96 (15)
C13—C14—H14A109.5C3—N2—H2118.5 (14)
C13—C14—H14B109.5N3—N2—H2117.5 (14)
H14A—C14—H14B109.5N2—N3—H3B103.8 (14)
C13—C14—H14C109.5N2—N3—H3A108.3 (16)
H14A—C14—H14C109.5H3B—N3—H3A112 (2)
H14B—C14—H14C109.5C22—N4—C27121.26 (14)
O5—C15—O4115.15 (15)C22—N4—C25121.55 (15)
O5—C15—C16127.16 (16)C27—N4—C25117.10 (15)
O4—C15—C16117.69 (14)C17—N5—N6122.83 (18)
C18—C16—C15118.90 (16)C17—N5—H5117.4 (15)
C18—C16—C17118.62 (16)N6—N5—H5119.7 (15)
C15—C16—C17122.48 (15)N5—N6—H6B108.7 (17)
O6—C17—N5121.62 (18)N5—N6—H6A106.1 (17)
O6—C17—C16120.77 (16)H6B—N6—H6A107 (2)
N5—C17—C16117.59 (17)C1—O1—C6122.45 (12)
C16—C18—C19122.60 (17)C15—O4—C20122.81 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O20.86 (3)2.01 (2)2.7098 (18)137 (2)
N5—H5···O50.87 (3)2.03 (2)2.733 (2)138 (2)
N6—H6B···O30.86 (3)2.30 (1)3.131 (2)164 (2)
N3—H3A···O3i0.87 (3)2.20 (1)3.002 (2)155 (2)
N3—H3B···O6ii0.87 (3)2.23 (1)3.039 (2)154 (2)
Symmetry codes: (i) −x, −y+1, −z+3; (ii) −x+1, −y+1, −z+3.
Table 1
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
N2—H2···O20.86 (3)2.01 (2)2.7098 (18)137 (2)
N5—H5···O50.87 (3)2.03 (2)2.733 (2)138 (2)
N6—H6B···O30.86 (3)2.30 (1)3.131 (2)164 (2)
N3—H3A···O3i0.87 (3)2.20 (1)3.002 (2)155 (2)
N3—H3B···O6ii0.87 (3)2.23 (1)3.039 (2)154 (2)
Symmetry codes: (i) −x, −y+1, −z+3; (ii) −x+1, −y+1, −z+3.
Acknowledgements top

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 21062022) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.

references
References top

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