(5-Hy­droxy-3-methyl-5-tri­fluoro­methyl-4,5-di­hydro-1H-pyrazol-1-yl)(2-hy­droxy­phen­yl)methanone

Avezov, K.G.; Umarov, B.B.; Talipov, S.A.; Kunafiev, R.J.; Ibragimov, B.T.

doi:10.1107/S2414314616003163

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160316

doi:10.1107/S2414314616003163

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(5-Hydroxy-3-methyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl)(2-hydroxyphenyl)methanone

Kuvondik G. Avezov,^a ^* Bako B. Umarov,^a Samat A. Talipov,^b Rishad J. Kunafiev ^b and Bakhtiyar T. Ibragimov ^b

^aBukhara State University, Department of Chemistry, M.Ikbol 11, Bukhara 200117, Uzbekistan, and ^bInstitute of Bioorganic Chemistry, Mirzo Ulugbek Str., 83, Tashkent 100125, Uzbekistan
^*Correspondence e-mail: avezovkg@mail.ru

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 January 2016; accepted 24 February 2016; online 2 March 2016)

In the title compound, C₁₂H₁₁F₃N₂O₃, the hydroxyphenyl ring is twisted by 35.42 (11)° from the plane of the pyrazoline ring. The keto O atom is involved in two intramolecular O—H⋯O hydrogen bonds, which generate S(6) loops. As result, a weak intramolecular C—H⋯N contact is formed, which generates an S(7) ring motif. In the crystal, pairs of O—H⋯O hydrogen bonds link molecules into inversion dimers with an R₂²(16) motif. The dimers are linked by parallel-slipped π–π interactions [intercentroid distance = 3.8438 (19) Å], forming columns along the c-axis direction.

Keywords: crystal structure; condensation; acylhydrazone; pyrazoline; O—H⋯O intramolecular hydrogen bonding.

CCDC reference: 1455362

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Chemical scheme

Structure description

Multifunctional ligands occupy a special place among the wide variety of organic ligands available (Filyakova et al., 2010 ; Chizhov et al., 2010 ; Chopin et al., 2012 ). It has been shown that formation of cyclic products depends on the location of the trifluoromethyl group in the intermediate, for example a hydrazone, where intramolecular cyclization is realized via multiple bonds near the trifluoromethyl substituent (Pakal'nis et al., 2008 ; 2014 ).

In the title compound, Fig. 1, the hydroxyphenyl ring (C5–C10) is twisted by 35.42 (11)° from the almost planar (r.m.s. deviation = 0.029 Å) pyrazoline ring (N1/N2/C1–C3). The keto-oxygen atom O2 acts as the acceptor for two intramolecular O1—H1⋯O2 and O3—H3⋯O2 hydrogen bonds (Table 1 and Fig. 1), which generate S(6) graph-set motifs. As a result, a weak intramolecular C10—H10⋯N2 contact is formed between atom N2 and a phenyl C—H group, which generates an S(7) graph-set motif (Fig. 1 and Table 1). In the crystal, pairs of O1—H1⋯O3ⁱ and O3—H3⋯O2ⁱ hydrogen bonds [symmetry code: (i) − x + 1, − y + 1, −z + 1] link molecules into inversion dimers, with an R₂²(16) ring motif for the former. The dimers stack along the c-axis direction, with parallel slipped π–π interactions [Cg2⋯Cg2ⁱ = 3.8438 (19) Å; inter-planar distance = 3.4798 (13) Å; slippage 1.633 Å; Cg2 is the centroid of ring C5–C10], forming columns (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.90 (4)	2.18 (5)	2.753 (3)	120 (4)
O3—H3⋯O2	0.97 (5)	1.71 (5)	2.562 (3)	144 (4)
C10—H10⋯N2	0.93	2.35	2.892 (4)	117
O1—H1⋯O3ⁱ	0.90 (4)	2.17 (5)	3.017 (3)	156 (5)
O3—H3⋯O2ⁱ	0.97 (5)	2.31 (4)	2.887 (3)	118 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Figure 1
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom labelling. Hydrogen bonds are shown as dashed lines (see Table 1

for details).

Figure 2
A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1

for details). For clarity, only the H atoms involved in hydrogen bonding have been included.

Synthesis and crystallization

The synthesis of the title compound is illustrated in Fig. 3. In a 100 ml flask were mixed 1,1,1-trifluoropentandione-2,4 (5 mmol) with benzoylhydrazine (5 mmol) in ethanol. The flask was connected to a return refrigerator and heated for 1 h in a water bath. The reaction progress was monitored by thin layer chromatography (Silufol UV-254 plates). On completion of the reaction, after several days, two thirds of the solvent was removed at room temperature. The crystalline solid that formed were filtered off, washed with ethanol and dried in a vacuum desiccator over P₂O₅ (yield 85%). The compound was further recrystallized from ethanol solution to obtain colourless block-like crystals of the title compound suitable for X-ray diffraction analysis.

Figure 3
Reaction scheme.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₁F₃N₂O₃
M_r	288.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.9339 (11), 10.6614 (9), 12.6802 (14)
β (°)	105.863 (11)
V (Å³)	1291.8 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.19
Crystal size (mm)	0.35 × 0.25 × 0.21

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ )
T_min, T_max	0.735, 0.779
No. of measured, independent and observed [I > 2σ(I)] reflections	4867, 2618, 1558
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.145, 1.04
No. of reflections	2618
No. of parameters	191
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21
Computer programs: (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ), OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1455362

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616003163/su4011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616003163/su4011Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616003163/su4011Isup3.cml

checkCIF report

Experimental top

The synthesis of the title compound is illustrated in Fig. 3. In a 100 ml flask were mixed 1,1,1-trifluoropentandione-2,4 (5 mmol) with benzoylhydrazine (5 mmol) in ethanol (?? ml). The flask was connected to a return refrigerator and heated for 1 h in a water bath. The reaction progress was monitored by thin layer chromatography (Silufol UV-254 plates). On completion of the reaction, after several days, two thirds of the solvent was removed at room temperature. The crystalline solid that formed were filtered off, washed with ethanol and dried in a vacuum desiccator over P₂O₅ (yield 85%). The compound was further recrystallized from ethanol to obtain colourless block-like crystals of the title compound suitable for X-ray diffraction analysis.

Structure description top

Multifunctional ligands occupy a special place among the wide variety of organic ligands available (Filyakova et al., 2010; Chizhov et al., 2010; Chopin et al., 2012). It has been shown that formation of cyclic products depends on the location of the trifluoromethyl group in the intermediate, for example a hydrazone, where intramolecular cyclization is realised via multiple bonds near the trifluoromethyl substituent (Pakal'nis et al., 2008; 2014).

In the title compound, Fig. 1, the hydroxyphenyl ring (C5–C10) is twisted by 35.42 (11)° from the planar (r.m.s. deviation = 0.029 Å) pyrazoline ring (N1/N2/C1–C3). The keto-oxygen atom O2 is involved in two intramolecular O1—H1···O2 and O3—H3···O2 hydrogen bonds (Table 1 and Fig. 1), which generate S(6) graph-set motifs. As a result, a weak intramolecular C10—H10···N2 contact is formed between atom N2 and a phenyl C—H group, which generates an S(7) graph-set motif (Fig. 1 and Table 1). In the crystal, pairs of O1—H1···O3ⁱ and O3—H3···O2ⁱ hydrogen bonds [symmetry code: (i) − x + 1, − y + 1, −z + 1] link molecules into inversion dimers, with an R²₂(16) ring motif for the former. The dimers stack along the c-axis direction, with parallel slipped π–π interactions [Cg2···Cg2ⁱ = 3.8438 (19) Å; inter-planar distance = 3.4798 (13) Å; slippage 1.633 Å; Cg2 is the centroid of ring C5–C10], forming columns.

Computing details top

Data collection: (CrysAlis PRO; Oxford Diffraction, 2009); cell refinement: (CrysAlis PRO; Oxford Diffraction, 2009); data reduction: (CrysAlis PRO; Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom labelling. Hydrogen bonds are shown as dashed lines (see Table 1 for details).
	Fig. 2. A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details). For clarity, only the H atoms involved in hydrogen bonding have been included.
	Fig. 3. Reaction scheme.

(5-Hydroxy-3-methyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl)(2-hydroxyphenyl)methanone top

Crystal data top

C₁₂H₁₁F₃N₂O₃	D_x = 1.482 Mg m⁻³
M_r = 288.23	Melting point: 401 K
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.9339 (11) Å	Cell parameters from 1180 reflections
b = 10.6614 (9) Å	θ = 4.1–72.2°
c = 12.6802 (14) Å	µ = 1.19 mm⁻¹
β = 105.863 (11)°	T = 293 K
V = 1291.8 (2) Å³	Block, colourless
Z = 4	0.35 × 0.25 × 0.21 mm
F(000) = 592

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2618 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1558 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 10.2576 pixels mm^-1	θ_max = 76.6°, θ_min = 3.6°
ω scans	h = −6→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
T_min = 0.735, T_max = 0.779	l = −15→15
4867 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.050	w = 1/[σ²(F_o²) + (0.0515P)² + 0.1383P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.145	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.22 e Å⁻³
2618 reflections	Δρ_min = −0.21 e Å⁻³
191 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0061 (6)

Crystal data top

C₁₂H₁₁F₃N₂O₃	V = 1291.8 (2) Å³
M_r = 288.23	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.9339 (11) Å	µ = 1.19 mm⁻¹
b = 10.6614 (9) Å	T = 293 K
c = 12.6802 (14) Å	0.35 × 0.25 × 0.21 mm
β = 105.863 (11)°

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2618 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1558 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.779	R_int = 0.035
4867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
2618 reflections	Δρ_min = −0.21 e Å⁻³
191 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
H1	−0.058 (5)	0.266 (4)	0.410 (4)	0.143 (18)*
H3	0.128 (5)	0.527 (4)	0.565 (4)	0.146 (18)*
C5	0.3393 (3)	0.4086 (2)	0.5730 (2)	0.0481 (6)
C4	0.2129 (3)	0.3490 (2)	0.5019 (2)	0.0487 (6)
C3	0.0914 (3)	0.1690 (2)	0.3879 (2)	0.0535 (7)
C6	0.3238 (3)	0.5213 (3)	0.6259 (2)	0.0609 (7)
C10	0.4745 (3)	0.3655 (3)	0.5839 (2)	0.0599 (7)
H10	0.4873	0.2927	0.5474	0.072*
C2	0.1335 (3)	0.0304 (2)	0.3972 (3)	0.0627 (8)
H2A	0.0640	−0.0206	0.4181	0.075*
H2B	0.1460	−0.0008	0.3287	0.075*
C1	0.2680 (3)	0.0313 (3)	0.4847 (3)	0.0608 (7)
C9	0.5902 (3)	0.4277 (3)	0.6473 (3)	0.0763 (9)
H9	0.6797	0.3971	0.6536	0.092*
C8	0.5714 (4)	0.5362 (3)	0.7015 (3)	0.0786 (10)
H8	0.6485	0.5780	0.7457	0.094*
C7	0.4395 (4)	0.5822 (3)	0.6902 (3)	0.0776 (9)
H7	0.4279	0.6555	0.7265	0.093*
C11	0.0791 (3)	0.2168 (3)	0.2723 (3)	0.0706 (8)
C12	0.3472 (4)	−0.0863 (3)	0.5260 (3)	0.0865 (11)
H12A	0.3759	−0.1255	0.4675	0.130*
H12B	0.2881	−0.1427	0.5522	0.130*
H12C	0.4282	−0.0662	0.5848	0.130*
N1	0.2131 (2)	0.22809 (18)	0.46637 (18)	0.0497 (5)
N2	0.3114 (2)	0.1391 (2)	0.52323 (19)	0.0560 (6)
O2	0.10240 (19)	0.40885 (17)	0.46969 (17)	0.0657 (6)
O1	−0.0347 (2)	0.1838 (2)	0.4140 (2)	0.0718 (6)
O3	0.1975 (3)	0.5737 (2)	0.6185 (2)	0.0906 (8)
F1	0.1990 (2)	0.20268 (19)	0.24635 (16)	0.0927 (7)
F3	0.0475 (3)	0.3363 (2)	0.25789 (17)	0.1146 (9)
F2	−0.0157 (2)	0.1509 (2)	0.19893 (18)	0.1155 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C5	0.0536 (14)	0.0397 (13)	0.0509 (15)	0.0009 (11)	0.0139 (11)	0.0015 (11)
C4	0.0544 (15)	0.0393 (12)	0.0548 (15)	0.0056 (11)	0.0189 (12)	−0.0014 (11)
C3	0.0513 (14)	0.0486 (15)	0.0621 (17)	0.0001 (12)	0.0179 (12)	−0.0088 (12)
C6	0.0677 (18)	0.0484 (15)	0.0673 (19)	0.0012 (14)	0.0194 (14)	−0.0081 (14)
C10	0.0573 (16)	0.0495 (15)	0.0723 (19)	0.0000 (13)	0.0166 (14)	−0.0001 (14)
C2	0.0694 (19)	0.0455 (15)	0.078 (2)	−0.0038 (13)	0.0273 (16)	−0.0105 (14)
C1	0.0650 (17)	0.0432 (14)	0.081 (2)	0.0036 (13)	0.0322 (15)	−0.0041 (14)
C9	0.0606 (19)	0.071 (2)	0.093 (2)	−0.0063 (16)	0.0129 (17)	0.0089 (19)
C8	0.081 (2)	0.076 (2)	0.071 (2)	−0.0271 (19)	0.0084 (17)	−0.0070 (18)
C7	0.092 (2)	0.0642 (19)	0.076 (2)	−0.0145 (19)	0.0220 (18)	−0.0174 (17)
C11	0.074 (2)	0.069 (2)	0.0622 (19)	0.0048 (17)	0.0065 (16)	−0.0126 (16)
C12	0.085 (2)	0.0457 (16)	0.131 (3)	0.0165 (16)	0.033 (2)	0.0042 (19)
N1	0.0540 (12)	0.0382 (10)	0.0545 (13)	0.0043 (9)	0.0107 (10)	−0.0043 (9)
N2	0.0562 (13)	0.0427 (12)	0.0690 (15)	0.0088 (10)	0.0167 (11)	0.0015 (11)
O2	0.0573 (11)	0.0486 (11)	0.0844 (14)	0.0132 (9)	0.0078 (10)	−0.0103 (10)
O1	0.0564 (12)	0.0602 (13)	0.1058 (17)	−0.0032 (10)	0.0342 (11)	−0.0122 (12)
O3	0.0792 (16)	0.0614 (14)	0.130 (2)	0.0081 (12)	0.0259 (15)	−0.0378 (14)
F1	0.1130 (16)	0.0994 (15)	0.0793 (14)	−0.0102 (13)	0.0490 (12)	−0.0106 (11)
F3	0.175 (2)	0.0846 (15)	0.0776 (14)	0.0470 (15)	0.0225 (14)	0.0188 (11)
F2	0.1112 (17)	0.142 (2)	0.0742 (13)	−0.0210 (15)	−0.0062 (12)	−0.0247 (14)

Geometric parameters (Å, º) top

C5—C4	1.475 (4)	C1—C12	1.497 (4)
C5—C6	1.405 (3)	C1—N2	1.277 (3)
C5—C10	1.390 (3)	C9—H9	0.9300
C4—N1	1.365 (3)	C9—C8	1.384 (4)
C4—O2	1.239 (3)	C8—H8	0.9300
C3—C2	1.532 (4)	C8—C7	1.370 (4)
C3—C11	1.525 (4)	C7—H7	0.9300
C3—N1	1.480 (3)	C11—F1	1.328 (4)
C3—O1	1.389 (3)	C11—F3	1.312 (4)
C6—C7	1.377 (4)	C11—F2	1.330 (3)
C6—O3	1.353 (3)	C12—H12A	0.9600
C10—H10	0.9300	C12—H12B	0.9600
C10—C9	1.379 (4)	C12—H12C	0.9600
C2—H2A	0.9700	N1—N2	1.411 (3)
C2—H2B	0.9700	O1—H1	0.90 (4)
C2—C1	1.486 (4)	O3—H3	0.97 (5)

C6—C5—C4	118.3 (2)	C10—C9—H9	120.4
C10—C5—C4	123.8 (2)	C10—C9—C8	119.2 (3)
C10—C5—C6	117.7 (3)	C8—C9—H9	120.4
N1—C4—C5	122.1 (2)	C9—C8—H8	119.9
O2—C4—C5	120.6 (2)	C7—C8—C9	120.2 (3)
O2—C4—N1	117.3 (2)	C7—C8—H8	119.9
C11—C3—C2	110.1 (2)	C6—C7—H7	119.6
N1—C3—C2	101.7 (2)	C8—C7—C6	120.9 (3)
N1—C3—C11	109.9 (2)	C8—C7—H7	119.6
O1—C3—C2	109.7 (2)	F1—C11—C3	111.0 (3)
O1—C3—C11	110.5 (2)	F1—C11—F2	106.2 (3)
O1—C3—N1	114.6 (2)	F3—C11—C3	114.3 (2)
C7—C6—C5	120.2 (3)	F3—C11—F1	105.8 (3)
O3—C6—C5	122.7 (3)	F3—C11—F2	108.6 (3)
O3—C6—C7	117.0 (3)	F2—C11—C3	110.6 (3)
C5—C10—H10	119.1	C1—C12—H12A	109.5
C9—C10—C5	121.8 (3)	C1—C12—H12B	109.5
C9—C10—H10	119.1	C1—C12—H12C	109.5
C3—C2—H2A	111.2	H12A—C12—H12B	109.5
C3—C2—H2B	111.2	H12A—C12—H12C	109.5
H2A—C2—H2B	109.1	H12B—C12—H12C	109.5
C1—C2—C3	102.8 (2)	C4—N1—C3	123.3 (2)
C1—C2—H2A	111.2	C4—N1—N2	122.0 (2)
C1—C2—H2B	111.2	N2—N1—C3	112.44 (19)
C2—C1—C12	122.3 (3)	C1—N2—N1	107.2 (2)
N2—C1—C2	115.6 (3)	C3—O1—H1	109 (3)
N2—C1—C12	122.0 (3)	C6—O3—H3	108 (3)

C5—C4—N1—C3	−174.9 (2)	C2—C3—N1—C4	−167.4 (2)
C5—C4—N1—N2	23.6 (3)	C2—C3—N1—N2	−4.4 (3)
C5—C6—C7—C8	1.7 (5)	C2—C1—N2—N1	−0.7 (3)
C5—C10—C9—C8	−0.2 (5)	C9—C8—C7—C6	0.5 (5)
C4—C5—C6—C7	−177.9 (3)	C11—C3—C2—C1	120.1 (3)
C4—C5—C6—O3	3.4 (4)	C11—C3—N1—C4	75.9 (3)
C4—C5—C10—C9	176.8 (3)	C11—C3—N1—N2	−121.1 (2)
C4—N1—N2—C1	166.7 (2)	C12—C1—N2—N1	179.9 (3)
C3—C2—C1—C12	177.4 (3)	N1—C3—C2—C1	3.6 (3)
C3—C2—C1—N2	−2.0 (3)	N1—C3—C11—F1	52.8 (3)
C3—N1—N2—C1	3.4 (3)	N1—C3—C11—F3	−66.8 (3)
C6—C5—C4—N1	−165.8 (2)	N1—C3—C11—F2	170.4 (2)
C6—C5—C4—O2	16.0 (4)	O2—C4—N1—C3	3.3 (4)
C6—C5—C10—C9	2.3 (4)	O2—C4—N1—N2	−158.2 (2)
C10—C5—C4—N1	19.8 (4)	O1—C3—C2—C1	−118.1 (3)
C10—C5—C4—O2	−158.4 (3)	O1—C3—C11—F1	−179.8 (2)
C10—C5—C6—C7	−3.1 (4)	O1—C3—C11—F3	60.7 (3)
C10—C5—C6—O3	178.1 (3)	O1—C3—C11—F2	−62.2 (3)
C10—C9—C8—C7	−1.3 (5)	O1—C3—N1—C4	−49.2 (3)
C2—C3—C11—F1	−58.4 (3)	O1—C3—N1—N2	113.8 (2)
C2—C3—C11—F3	−178.0 (3)	O3—C6—C7—C8	−179.4 (3)
C2—C3—C11—F2	59.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.90 (4)	2.18 (5)	2.753 (3)	120 (4)
O3—H3···O2	0.97 (5)	1.71 (5)	2.562 (3)	144 (4)
C10—H10···N2	0.93	2.35	2.892 (4)	117
O1—H1···O3ⁱ	0.90 (4)	2.17 (5)	3.017 (3)	156 (5)
O3—H3···O2ⁱ	0.97 (5)	2.31 (4)	2.887 (3)	118 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.90 (4)	2.18 (5)	2.753 (3)	120 (4)
O3—H3···O2	0.97 (5)	1.71 (5)	2.562 (3)	144 (4)
C10—H10···N2	0.93	2.35	2.892 (4)	117
O1—H1···O3ⁱ	0.90 (4)	2.17 (5)	3.017 (3)	156 (5)
O3—H3···O2ⁱ	0.97 (5)	2.31 (4)	2.887 (3)	118 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁F₃N₂O₃
M_r	288.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.9339 (11), 10.6614 (9), 12.6802 (14)
β (°)	105.863 (11)
V (Å³)	1291.8 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.19
Crystal size (mm)	0.35 × 0.25 × 0.21

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.735, 0.779
No. of measured, independent and observed [I > 2σ(I)] reflections	4867, 2618, 1558
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.145, 1.04
No. of reflections	2618
No. of parameters	191
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: (CrysAlis PRO; Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), Mercury (Macrae et al., 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

This work was supported by the Uzbekistan Foundation for Basic Research (project OT-F3–012).

References

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