3-{1-[2-(2-Chloro­phen­yl)hydrazinyl­idene]-2,2,2-trifluoro­eth­yl}-7-diethyl­amino-2H-chromen-2-one

Chen, H.; Cai, L.; Yu, C.; Li, H.

doi:10.1107/S1600536811031916

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2344

doi:10.1107/S1600536811031916

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3-{1-[2-(2-Chlorophenyl)hydrazinylidene]-2,2,2-trifluoroethyl}-7-diethylamino-2H-chromen-2-one

Hao Chen,^a Li Cai,^a Chaochao Yu ^a and Hongqi Li ^a ^*

^aKey Laboratory of Science & Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering & Biotechnology, Donghua University, Shanghai 201620, People's Republic of China
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 18 July 2011; accepted 7 August 2011; online 17 August 2011)

The title compound, C₂₁H₁₉ClF₃N₃O₂, has a structure related to other coumarin derivatives that have been used as fluorescent probes of metal ions. The dihedral angle between the coumarin ring system and the chlorobenzene ring is 42.99 (9)°. Intramolecular hydrogen bonding occurs via N—H⋯O and N—H⋯Cl interactions, generating S(7) and S(5) rings, respectively. The crystal packing is stabilized by weak C—H⋯O hydrogen bonds.

Related literature

For applications of coumarins and coumarin derivatives, see: Trenor et al. (2004 ); Starcevic et al. (2011 ); Danko et al. (2011 ). For the synthesis of the title compound and related structures, see: Li et al. (2011 ).

Experimental

Crystal data

C₂₁H₁₉ClF₃N₃O₂
M_r = 437.84
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.940 (6) Å
b = 12.602 (9) Å
c = 20.233 (15) Å
V = 2025 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.954, T_max = 0.958
10369 measured reflections
3576 independent reflections
3162 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.078
S = 1.03
3576 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1511 Friedel pairs
Flack parameter: −0.09 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl1	0.86	2.57	2.960 (2)	109
N3—H3A⋯O2	0.86	2.22	2.761 (3)	121
C14—H14⋯O2ⁱ	0.93	2.55	3.316 (3)	140
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031916/lr2022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031916/lr2022Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031916/lr2022Isup3.cml

checkCIF report

Comment top

Because the structure of benzopyrone has many advantages including high fluorescence quantum yield, large Stokes shift, excellent light stability, and less toxicity coumairns have been widely used in the fields of biology, medicine (Starcevic et al., 2011), perfumes, cosmetics (Trenor et al., 2004), and fluorescent dyes (Danko et al., 2011). We have synthesized a series of novel coumarin derivatives and found that one of them 3-(2-benzoylhydrazonotrifluoroethyl)-7- (N,N-diethylamino)coumarin can be used as fluorescent probes of Cu(II) and Ni(II) (Li et al., 2011). Herein we report the single-crystal structure of 3-(2-Chlorophenylhydrazonotrifluoroethyl)-7-(N,N- diethylamino)coumarin, which may be a good candidate for fluorescent probe of metal ions.

Related literature top

For applications of coumarins and coumarin derivatives, see: Trenor et al. (2004); Starcevic et al. (2011); Danko et al. (2011). For the synthesis of the title compound and related structures, see: Li et al. (2011).

Experimental top

The title compound was prepared as reported in the literature (Li et al., 2011). Red orange single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from a 1:1 petroleum ether and ethyl acetate mixture.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP plot of the title compound with displacement ellipsoids at the 30% probability level. H atoms are omitted for clarity.

3-{1-[2-(2-Chlorophenyl)hydrazinylidene]-2,2,2-trifluoroethyl}- 7-diethylamino-2H-chromen-2-one top

Crystal data top

C₂₁H₁₉ClF₃N₃O₂	D_x = 1.436 Mg m⁻³
M_r = 437.84	Melting point = 423–425 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.940 (6) Å	Cell parameters from 3770 reflections
b = 12.602 (9) Å	θ = 2.6–24.7°
c = 20.233 (15) Å	µ = 0.24 mm⁻¹
V = 2025 (3) Å³	T = 296 K
Z = 4	Block, orange
F(000) = 904	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	3576 independent reflections
Radiation source: fine-focus sealed tube	3162 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.954, T_max = 0.958	k = −15→9
10369 measured reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0416P)² + 0.1045P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3576 reflections	Δρ_max = 0.15 e Å⁻³
273 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1511 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (6)

Crystal data top

C₂₁H₁₉ClF₃N₃O₂	V = 2025 (3) Å³
M_r = 437.84	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.940 (6) Å	µ = 0.24 mm⁻¹
b = 12.602 (9) Å	T = 296 K
c = 20.233 (15) Å	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	3576 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3162 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.958	R_int = 0.023
10369 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.15 e Å⁻³
S = 1.03	Δρ_min = −0.21 e Å⁻³
3576 reflections	Absolute structure: Flack (1983), 1511 Friedel pairs
273 parameters	Absolute structure parameter: −0.09 (6)
0 restraints

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

	x	y	z	U_iso*/U_eq
C1	−0.0571 (3)	0.51038 (15)	0.15673 (9)	0.0426 (5)
C2	−0.0012 (3)	0.46256 (15)	0.09683 (10)	0.0479 (5)
H2	0.0292	0.3913	0.0970	0.058*
C3	0.0088 (3)	0.51828 (14)	0.03965 (10)	0.0450 (5)
H3	0.0447	0.4842	0.0014	0.054*
C4	−0.0343 (2)	0.62689 (14)	0.03692 (9)	0.0382 (4)
C5	−0.0249 (2)	0.69109 (14)	−0.01980 (10)	0.0391 (4)
H5	0.0082	0.6604	−0.0595	0.047*
C6	−0.0629 (2)	0.79729 (14)	−0.01872 (9)	0.0358 (4)
C7	−0.1134 (3)	0.84426 (14)	0.04343 (9)	0.0392 (4)
C8	−0.0900 (2)	0.67227 (13)	0.09569 (9)	0.0366 (4)
C9	−0.1056 (3)	0.61729 (14)	0.15382 (9)	0.0415 (5)
H9	−0.1481	0.6508	0.1912	0.050*
C10	−0.0636 (2)	0.86150 (14)	−0.08005 (8)	0.0363 (4)
C11	0.1033 (2)	1.12141 (14)	−0.06355 (9)	0.0382 (4)
C12	0.1722 (3)	1.18859 (16)	−0.01670 (10)	0.0471 (5)
C13	0.2242 (3)	1.29033 (17)	−0.03257 (12)	0.0564 (6)
H13	0.2701	1.3341	−0.0003	0.068*
C14	0.2075 (3)	1.32630 (17)	−0.09657 (12)	0.0613 (6)
H14	0.2430	1.3942	−0.1080	0.074*
C15	0.1377 (3)	1.26061 (16)	−0.14320 (11)	0.0559 (6)
H15	0.1242	1.2851	−0.1862	0.067*
C16	0.0874 (3)	1.15921 (15)	−0.12760 (10)	0.0456 (5)
H16	0.0424	1.1157	−0.1603	0.055*
C17	−0.1226 (3)	0.80735 (15)	−0.14206 (10)	0.0434 (5)
C18	0.0107 (3)	0.34867 (17)	0.21991 (12)	0.0607 (6)
H18A	−0.0171	0.3080	0.1807	0.073*
H18B	−0.0374	0.3124	0.2578	0.073*
C19	0.1987 (3)	0.3531 (2)	0.22744 (16)	0.0921 (9)
H19A	0.2465	0.3907	0.1907	0.138*
H19B	0.2431	0.2823	0.2287	0.138*
H19C	0.2266	0.3892	0.2678	0.138*
C20	−0.1199 (3)	0.50530 (18)	0.27618 (10)	0.0596 (6)
H20A	−0.0763	0.5772	0.2778	0.071*
H20B	−0.0738	0.4667	0.3135	0.071*
C21	−0.3098 (3)	0.50846 (19)	0.28210 (12)	0.0698 (7)
H21A	−0.3558	0.5489	0.2462	0.105*
H21B	−0.3405	0.5411	0.3233	0.105*
H21C	−0.3535	0.4375	0.2807	0.105*
Cl1	0.19498 (10)	1.14505 (5)	0.06447 (3)	0.0753 (2)
F1	−0.24651 (16)	0.73715 (9)	−0.13101 (6)	0.0567 (3)
F2	0.00093 (17)	0.75115 (10)	−0.17132 (6)	0.0632 (4)
F3	−0.17985 (19)	0.87363 (10)	−0.18810 (5)	0.0661 (4)
N1	−0.0641 (2)	0.45457 (13)	0.21455 (9)	0.0514 (4)
N2	−0.0139 (2)	0.95674 (12)	−0.09268 (8)	0.0397 (4)
N3	0.0552 (2)	1.01831 (12)	−0.04584 (8)	0.0437 (4)
H3A	0.0694	0.9952	−0.0062	0.052*
O1	−0.12920 (18)	0.77888 (9)	0.09745 (6)	0.0415 (3)
O2	−0.1471 (2)	0.93702 (10)	0.05297 (6)	0.0522 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0369 (11)	0.0411 (11)	0.0499 (11)	−0.0028 (9)	−0.0021 (9)	0.0060 (9)
C2	0.0502 (13)	0.0323 (10)	0.0613 (12)	0.0059 (10)	0.0028 (11)	0.0016 (9)
C3	0.0496 (12)	0.0335 (10)	0.0520 (11)	0.0050 (9)	0.0082 (10)	−0.0049 (9)
C4	0.0382 (11)	0.0322 (9)	0.0441 (10)	0.0007 (8)	0.0012 (8)	−0.0024 (8)
C5	0.0382 (11)	0.0361 (10)	0.0430 (10)	0.0023 (8)	0.0020 (9)	−0.0069 (8)
C6	0.0337 (10)	0.0334 (9)	0.0404 (10)	−0.0007 (8)	0.0015 (8)	−0.0041 (8)
C7	0.0395 (11)	0.0338 (10)	0.0441 (10)	0.0006 (9)	0.0034 (9)	−0.0006 (8)
C8	0.0356 (11)	0.0283 (9)	0.0458 (11)	0.0003 (8)	−0.0020 (9)	−0.0039 (8)
C9	0.0448 (12)	0.0373 (10)	0.0423 (11)	−0.0002 (9)	0.0035 (9)	−0.0008 (8)
C10	0.0359 (11)	0.0332 (10)	0.0398 (10)	0.0001 (8)	−0.0001 (8)	−0.0045 (8)
C11	0.0341 (11)	0.0338 (9)	0.0467 (10)	0.0001 (8)	0.0010 (9)	−0.0045 (9)
C12	0.0439 (12)	0.0480 (12)	0.0493 (11)	−0.0006 (9)	−0.0033 (10)	−0.0109 (9)
C13	0.0489 (14)	0.0448 (12)	0.0755 (15)	−0.0057 (11)	0.0002 (12)	−0.0199 (11)
C14	0.0652 (17)	0.0379 (11)	0.0809 (16)	−0.0099 (11)	0.0106 (14)	−0.0033 (12)
C15	0.0653 (15)	0.0442 (12)	0.0584 (12)	−0.0021 (11)	0.0072 (12)	0.0072 (11)
C16	0.0494 (12)	0.0402 (11)	0.0470 (11)	−0.0022 (9)	0.0002 (10)	−0.0045 (9)
C17	0.0439 (12)	0.0416 (10)	0.0448 (11)	0.0006 (10)	0.0007 (10)	−0.0035 (9)
C18	0.0596 (15)	0.0501 (13)	0.0723 (14)	0.0051 (12)	0.0076 (13)	0.0251 (12)
C19	0.0581 (18)	0.098 (2)	0.120 (2)	0.0182 (16)	0.0011 (17)	0.0512 (19)
C20	0.0794 (18)	0.0557 (13)	0.0437 (12)	0.0008 (13)	−0.0060 (11)	0.0080 (10)
C21	0.0807 (19)	0.0722 (16)	0.0566 (14)	0.0012 (15)	0.0098 (13)	0.0013 (12)
Cl1	0.0938 (5)	0.0819 (4)	0.0501 (3)	−0.0075 (4)	−0.0206 (3)	−0.0080 (3)
F1	0.0522 (7)	0.0562 (7)	0.0616 (7)	−0.0130 (6)	−0.0040 (6)	−0.0129 (6)
F2	0.0581 (8)	0.0710 (8)	0.0604 (7)	0.0048 (7)	0.0106 (6)	−0.0272 (6)
F3	0.0926 (11)	0.0582 (8)	0.0474 (7)	0.0008 (7)	−0.0190 (7)	−0.0007 (6)
N1	0.0567 (12)	0.0434 (9)	0.0542 (10)	0.0047 (9)	0.0003 (9)	0.0121 (8)
N2	0.0408 (10)	0.0356 (9)	0.0429 (8)	0.0006 (7)	0.0006 (7)	−0.0048 (7)
N3	0.0537 (11)	0.0375 (8)	0.0398 (9)	−0.0064 (8)	−0.0056 (7)	−0.0017 (7)
O1	0.0534 (9)	0.0311 (6)	0.0401 (7)	0.0056 (6)	0.0076 (6)	−0.0014 (6)
O2	0.0747 (11)	0.0300 (7)	0.0519 (8)	0.0090 (7)	0.0138 (8)	−0.0026 (6)

Geometric parameters (Å, º) top

C1—N1	1.366 (3)	C13—H13	0.9300
C1—C9	1.402 (3)	C14—C15	1.372 (3)
C1—C2	1.424 (3)	C14—H14	0.9300
C2—C3	1.356 (3)	C15—C16	1.376 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.412 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—F3	1.331 (2)
C4—C8	1.392 (3)	C17—F1	1.342 (2)
C4—C5	1.406 (3)	C17—F2	1.347 (2)
C5—C6	1.372 (3)	C18—N1	1.465 (3)
C5—H5	0.9300	C18—C19	1.501 (4)
C6—C7	1.447 (3)	C18—H18A	0.9700
C6—C10	1.481 (3)	C18—H18B	0.9700
C7—O2	1.215 (2)	C19—H19A	0.9600
C7—O1	1.374 (2)	C19—H19B	0.9600
C8—C9	1.371 (3)	C19—H19C	0.9600
C8—O1	1.380 (2)	C20—N1	1.470 (3)
C9—H9	0.9300	C20—C21	1.513 (4)
C10—N2	1.289 (2)	C20—H20A	0.9700
C10—C17	1.503 (3)	C20—H20B	0.9700
C11—C12	1.384 (3)	C21—H21A	0.9600
C11—C16	1.387 (3)	C21—H21B	0.9600
C11—N3	1.401 (2)	C21—H21C	0.9600
C12—C13	1.385 (3)	N2—N3	1.342 (2)
C12—Cl1	1.741 (2)	N3—H3A	0.8600
C13—C14	1.378 (3)

N1—C1—C9	121.30 (18)	C14—C15—H15	119.3
N1—C1—C2	121.56 (18)	C16—C15—H15	119.3
C9—C1—C2	117.14 (17)	C15—C16—C11	120.48 (19)
C3—C2—C1	121.68 (18)	C15—C16—H16	119.8
C3—C2—H2	119.2	C11—C16—H16	119.8
C1—C2—H2	119.2	F3—C17—F1	106.26 (17)
C2—C3—C4	121.42 (17)	F3—C17—F2	105.71 (17)
C2—C3—H3	119.3	F1—C17—F2	105.10 (15)
C4—C3—H3	119.3	F3—C17—C10	113.93 (16)
C8—C4—C5	118.53 (16)	F1—C17—C10	112.88 (16)
C8—C4—C3	116.23 (16)	F2—C17—C10	112.26 (17)
C5—C4—C3	125.24 (17)	N1—C18—C19	112.1 (2)
C6—C5—C4	122.46 (18)	N1—C18—H18A	109.2
C6—C5—H5	118.8	C19—C18—H18A	109.2
C4—C5—H5	118.8	N1—C18—H18B	109.2
C5—C6—C7	118.29 (18)	C19—C18—H18B	109.2
C5—C6—C10	121.36 (17)	H18A—C18—H18B	107.9
C7—C6—C10	120.22 (16)	C18—C19—H19A	109.5
O2—C7—O1	115.49 (16)	C18—C19—H19B	109.5
O2—C7—C6	126.37 (17)	H19A—C19—H19B	109.5
O1—C7—C6	118.12 (15)	C18—C19—H19C	109.5
C9—C8—O1	116.72 (16)	H19A—C19—H19C	109.5
C9—C8—C4	123.65 (17)	H19B—C19—H19C	109.5
O1—C8—C4	119.61 (16)	N1—C20—C21	112.3 (2)
C8—C9—C1	119.79 (17)	N1—C20—H20A	109.1
C8—C9—H9	120.1	C21—C20—H20A	109.1
C1—C9—H9	120.1	N1—C20—H20B	109.1
N2—C10—C6	132.33 (16)	C21—C20—H20B	109.1
N2—C10—C17	110.65 (16)	H20A—C20—H20B	107.9
C6—C10—C17	116.90 (16)	C20—C21—H21A	109.5
C12—C11—C16	117.78 (18)	C20—C21—H21B	109.5
C12—C11—N3	120.01 (18)	H21A—C21—H21B	109.5
C16—C11—N3	122.20 (17)	C20—C21—H21C	109.5
C11—C12—C13	121.7 (2)	H21A—C21—H21C	109.5
C11—C12—Cl1	119.64 (16)	H21B—C21—H21C	109.5
C13—C12—Cl1	118.65 (17)	C1—N1—C18	121.08 (18)
C14—C13—C12	119.6 (2)	C1—N1—C20	120.98 (17)
C14—C13—H13	120.2	C18—N1—C20	117.11 (18)
C12—C13—H13	120.2	C10—N2—N3	121.57 (16)
C15—C14—C13	119.1 (2)	N2—N3—C11	117.85 (16)
C15—C14—H14	120.4	N2—N3—H3A	121.1
C13—C14—H14	120.4	C11—N3—H3A	121.1
C14—C15—C16	121.3 (2)	C7—O1—C8	122.86 (14)

N1—C1—C2—C3	−178.8 (2)	Cl1—C12—C13—C14	179.90 (18)
C9—C1—C2—C3	1.5 (3)	C12—C13—C14—C15	0.7 (4)
C1—C2—C3—C4	0.7 (3)	C13—C14—C15—C16	−1.3 (4)
C2—C3—C4—C8	−1.1 (3)	C14—C15—C16—C11	1.2 (3)
C2—C3—C4—C5	178.8 (2)	C12—C11—C16—C15	−0.5 (3)
C8—C4—C5—C6	2.4 (3)	N3—C11—C16—C15	−179.3 (2)
C3—C4—C5—C6	−177.6 (2)	N2—C10—C17—F3	−27.1 (2)
C4—C5—C6—C7	0.3 (3)	C6—C10—C17—F3	156.38 (17)
C4—C5—C6—C10	−175.63 (17)	N2—C10—C17—F1	−148.43 (17)
C5—C6—C7—O2	178.2 (2)	C6—C10—C17—F1	35.1 (2)
C10—C6—C7—O2	−5.8 (3)	N2—C10—C17—F2	93.0 (2)
C5—C6—C7—O1	−3.3 (3)	C6—C10—C17—F2	−83.5 (2)
C10—C6—C7—O1	172.71 (16)	C9—C1—N1—C18	−170.4 (2)
C5—C4—C8—C9	179.41 (19)	C2—C1—N1—C18	9.9 (3)
C3—C4—C8—C9	−0.6 (3)	C9—C1—N1—C20	−1.1 (3)
C5—C4—C8—O1	−2.0 (3)	C2—C1—N1—C20	179.2 (2)
C3—C4—C8—O1	177.93 (18)	C19—C18—N1—C1	77.9 (3)
O1—C8—C9—C1	−175.76 (18)	C19—C18—N1—C20	−91.8 (3)
C4—C8—C9—C1	2.8 (3)	C21—C20—N1—C1	82.7 (3)
N1—C1—C9—C8	177.09 (18)	C21—C20—N1—C18	−107.6 (2)
C2—C1—C9—C8	−3.2 (3)	C6—C10—N2—N3	0.4 (3)
C5—C6—C10—N2	−140.5 (2)	C17—C10—N2—N3	−175.39 (17)
C7—C6—C10—N2	43.6 (3)	C10—N2—N3—C11	−178.98 (17)
C5—C6—C10—C17	35.1 (3)	C12—C11—N3—N2	178.80 (17)
C7—C6—C10—C17	−140.80 (19)	C16—C11—N3—N2	−2.4 (3)
C16—C11—C12—C13	−0.1 (3)	O2—C7—O1—C8	−177.57 (17)
N3—C11—C12—C13	178.75 (19)	C6—C7—O1—C8	3.7 (3)
C16—C11—C12—Cl1	−179.98 (15)	C9—C8—O1—C7	177.61 (18)
N3—C11—C12—Cl1	−1.2 (3)	C4—C8—O1—C7	−1.1 (3)
C11—C12—C13—C14	0.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1	0.86	2.57	2.960 (2)	109
N3—H3A···O2	0.86	2.22	2.761 (3)	121
C14—H14···O2ⁱ	0.93	2.55	3.316 (3)	140

Symmetry code: (i) x+1/2, −y+5/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉ClF₃N₃O₂
M_r	437.84
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.940 (6), 12.602 (9), 20.233 (15)
V (Å³)	2025 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.954, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	10369, 3576, 3162
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.078, 1.03
No. of reflections	3576
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21
Absolute structure	Flack (1983), 1511 Friedel pairs
Absolute structure parameter	−0.09 (6)

Computer programs: APEX2 (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1	0.86	2.57	2.960 (2)	108.7
N3—H3A···O2	0.86	2.22	2.761 (3)	120.8
C14—H14···O2ⁱ	0.93	2.55	3.316 (3)	139.5

Symmetry code: (i) x+1/2, −y+5/2, −z.

Acknowledgements

Financial support by the Fundamental Research Funds for the Central Universities was acknowledged.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Danko, M., Szabo, E. & Hrdlovic, P. (2011). Dyes Pigments, 90, 129–138. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, H., Cai, L., Li, J., Hu, Y., Zhou, P. & Zhang, J. (2011). Dyes Pigments, 91, 309–316. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Starcevic, S., Brozic, P., Turk, S., Cesar, J., Lanisnik Rizner, T. & Gobec, S. (2011). J. Med. Chem. 54, 248–261. Google Scholar
Trenor, S. R., Shultz, A. R., Love, B. J. & Long, T. E. (2004). Chem. Rev. 104, 3059–3077. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 67| Part 9| September 2011| Page o2344

doi:10.1107/S1600536811031916

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-{1-[2-(2-Chloro­phen­yl)hydrazinyl­­idene]-2,2,2-tri­fluoro­eth­yl}-7-di­ethyl­amino-2H-chromen-2-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-{1-[2-(2-Chlorophenyl)hydrazinylidene]-2,2,2-trifluoroethyl}-7-diethylamino-2H-chromen-2-one