Literature DB >> 21754425

7-Diethyl-amino-2-oxo-2H-chromene-3-carbohydrazide.

Li-Jun Zhang1, Bing-Zhu Yin.   

Abstract

The asymmetric unit of the title compound, C(14)H(17)N(3)O(3), contains two independent mol-ecules with different conformations of the ethyl groups. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into ribbons extending along the a axis.

Entities:  

Year:  2011        PMID: 21754425      PMCID: PMC3089128          DOI: 10.1107/S1600536811010944

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

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

Crystal data

C14H17N3O3 M = 275.31 Triclinic, a = 9.3438 (19) Å b = 12.771 (3) Å c = 12.978 (3) Å α = 95.17 (3)° β = 110.13 (3)° γ = 106.18 (3)° V = 1366.4 (5) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 290 K 0.14 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.987, T max = 0.990 13506 measured reflections 6186 independent reflections 3402 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.117 S = 1.01 6186 reflections 383 parameters 6 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.18 e Å−3 Δρmin = −0.19 e Å−3 Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ▶); cell refinement: RAPID-AUTO; 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010944/cv5061sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010944/cv5061Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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
Rigaku R-AXIS RAPID diffractometer6186 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 = −12→10
Tmin = 0.987, Tmax = 0.990k = −16→16
13506 measured reflectionsl = −16→16
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 = 1.01w = 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
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.
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)
H9−0.01440.14890.87540.063*
C100.01086 (19)0.24390 (13)1.01450 (14)0.0516 (4)
H10−0.04430.18551.03910.062*
C110.0769 (2)0.17291 (15)0.71424 (16)0.0645 (5)
H11A0.09600.12390.76660.077*
H11B0.14110.16990.66980.077*
C12−0.0988 (2)0.13259 (17)0.63824 (16)0.0768 (6)
H12A−0.16250.13750.68170.115*
H12B−0.12950.05650.60130.115*
H12C−0.11680.17800.58320.115*
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)
H210.2345−0.04540.89620.061*
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)
H25A0.5055−0.03860.66390.082*
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)
H27A0.2679−0.15510.78370.078*
H27B0.2989−0.16270.67270.078*
C280.1023 (2)−0.11651 (16)0.65768 (16)0.0717 (5)
H28A0.0664−0.08110.70770.108*
H28B0.0299−0.19150.62530.108*
H28C0.1040−0.07580.59920.108*
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)
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)
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)
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)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—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) ; (ii) .

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