1-[2,6-Dichloro-4-(trifluoro-meth-yl)phen-yl]-3,4-dimethyl-pyrano[2,3-c]pyrazol-6(1H)-one.

In the title compound, C(15)H(9)Cl(2)F(3)N(2)O(2), the 1,6-dihydro-pyrano[2,3-c]pyrazole ring system is almost planar, with a maximum deviation of 0.0226 (14) Å, and forms a dihedral angle of 69.90 (6)° with the benzene ring. In the crystal, mol-ecules are linked into a helical chain along the c axis by C-H⋯O hydrogen bonds.

Related literature

For background to and the biological activity of pyrazolone derivatives, see: Kokura et al. (2005 ▶); Sarojini et al. (2010 ▶); Vaid et al. (1986 ▶). For related structures, see: Ramsay & Steel (1985 ▶); Ahmad et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H9Cl2F3N2O2

M = 377.14

Orthorhombic,

a = 13.3348 (2) Å

b = 14.2045 (2) Å

c = 15.9132 (3) Å

V = 3014.19 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.48 mm−1

T = 100 K

0.44 × 0.31 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.819, T max = 0.888

24894 measured reflections

4382 independent reflections

3706 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.03

4382 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029789/is5160sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029789/is5160Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029789/is5160Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H9Cl2F3N2O2	F(000) = 1520
Mr = 377.14	Dx = 1.662 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9873 reflections
a = 13.3348 (2) Å	θ = 2.5–32.6°
b = 14.2045 (2) Å	µ = 0.48 mm−1
c = 15.9132 (3) Å	T = 100 K
V = 3014.19 (8) Å3	Block, orange
Z = 8	0.44 × 0.31 × 0.26 mm

Bruker SMART APEXII CCD area-detector diffractometer	4382 independent reflections
Radiation source: fine-focus sealed tube	3706 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.819, Tmax = 0.888	k = −19→19
24894 measured reflections	l = −22→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0445P)2 + 2.1563P] where P = (Fo2 + 2Fc2)/3
4382 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Cl1	0.05786 (3)	0.14096 (3)	0.71268 (2)	0.02478 (10)
Cl2	0.32815 (3)	0.42169 (3)	0.68567 (2)	0.02497 (10)
F1	0.01024 (12)	0.35846 (9)	0.97088 (8)	0.0559 (4)
F2	0.14301 (8)	0.44227 (10)	0.97926 (7)	0.0426 (3)
F3	0.01721 (9)	0.49137 (8)	0.91002 (6)	0.0399 (3)
O1	0.20606 (8)	0.33302 (7)	0.52607 (6)	0.0197 (2)
O2	0.18623 (9)	0.41836 (8)	0.41029 (7)	0.0260 (2)
N1	0.29995 (9)	0.15794 (8)	0.66209 (8)	0.0187 (2)
N2	0.23949 (9)	0.23515 (8)	0.64239 (7)	0.0181 (2)
C1	0.23104 (11)	0.35320 (10)	0.44100 (9)	0.0202 (3)
C2	0.30521 (11)	0.29344 (10)	0.40143 (9)	0.0209 (3)
H2A	0.3237	0.3070	0.3451	0.025*
C3	0.35023 (11)	0.21887 (10)	0.43997 (9)	0.0189 (3)
C4	0.32303 (10)	0.20139 (10)	0.52589 (9)	0.0166 (3)
C5	0.34852 (11)	0.13725 (10)	0.59193 (9)	0.0180 (3)
C6	0.25427 (11)	0.26101 (9)	0.56213 (9)	0.0174 (3)
C7	0.19107 (10)	0.28382 (9)	0.70869 (9)	0.0167 (3)
C8	0.10967 (10)	0.24338 (9)	0.75021 (9)	0.0173 (2)
C9	0.06951 (11)	0.28556 (10)	0.82140 (9)	0.0184 (3)
H9A	0.0149	0.2574	0.8503	0.022*
C10	0.11052 (11)	0.36948 (10)	0.84946 (9)	0.0176 (3)
C11	0.18835 (11)	0.41405 (10)	0.80713 (9)	0.0189 (3)
H11A	0.2135	0.4730	0.8258	0.023*
C12	0.22825 (10)	0.37016 (10)	0.73692 (9)	0.0179 (3)
C13	0.42522 (12)	0.15731 (12)	0.39669 (10)	0.0247 (3)
H13A	0.4314	0.1766	0.3378	0.037*
H13B	0.4029	0.0916	0.3994	0.037*
H13C	0.4905	0.1634	0.4245	0.037*
C14	0.41785 (12)	0.05479 (11)	0.59007 (10)	0.0227 (3)
H14A	0.4190	0.0247	0.6455	0.034*
H14B	0.4856	0.0761	0.5755	0.034*
H14C	0.3946	0.0094	0.5480	0.034*
C15	0.07067 (11)	0.41500 (10)	0.92787 (9)	0.0199 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.02666 (18)	0.01914 (17)	0.02854 (19)	−0.00419 (13)	0.00424 (15)	−0.00636 (13)
Cl2	0.02532 (18)	0.02462 (18)	0.02499 (19)	−0.00624 (13)	0.00913 (14)	−0.00204 (13)
F1	0.0876 (10)	0.0374 (6)	0.0427 (7)	−0.0230 (6)	0.0449 (7)	−0.0153 (5)
F2	0.0261 (5)	0.0781 (9)	0.0235 (5)	0.0124 (5)	−0.0059 (4)	−0.0203 (5)
F3	0.0531 (7)	0.0427 (6)	0.0240 (5)	0.0310 (5)	−0.0038 (5)	−0.0093 (4)
O1	0.0229 (5)	0.0196 (5)	0.0166 (5)	0.0040 (4)	0.0025 (4)	0.0000 (4)
O2	0.0315 (6)	0.0244 (5)	0.0221 (5)	0.0033 (4)	0.0003 (5)	0.0033 (4)
N1	0.0205 (6)	0.0167 (5)	0.0190 (6)	0.0034 (4)	0.0012 (5)	−0.0010 (4)
N2	0.0219 (6)	0.0168 (5)	0.0156 (5)	0.0033 (4)	0.0039 (5)	−0.0012 (4)
C1	0.0234 (7)	0.0205 (6)	0.0169 (6)	−0.0023 (5)	0.0004 (5)	0.0000 (5)
C2	0.0216 (7)	0.0246 (7)	0.0166 (6)	−0.0021 (5)	0.0025 (5)	−0.0023 (5)
C3	0.0173 (6)	0.0214 (6)	0.0180 (6)	−0.0031 (5)	0.0024 (5)	−0.0052 (5)
C4	0.0160 (6)	0.0171 (6)	0.0168 (6)	−0.0003 (5)	0.0019 (5)	−0.0028 (5)
C5	0.0174 (6)	0.0169 (6)	0.0196 (7)	−0.0006 (5)	0.0001 (5)	−0.0037 (5)
C6	0.0193 (6)	0.0162 (6)	0.0167 (6)	0.0000 (5)	0.0014 (5)	−0.0017 (5)
C7	0.0182 (6)	0.0171 (6)	0.0147 (6)	0.0033 (5)	0.0013 (5)	−0.0016 (5)
C8	0.0181 (6)	0.0158 (6)	0.0179 (6)	0.0003 (5)	−0.0001 (5)	−0.0013 (5)
C9	0.0181 (6)	0.0190 (6)	0.0182 (6)	0.0014 (5)	0.0029 (5)	0.0007 (5)
C10	0.0195 (6)	0.0180 (6)	0.0152 (6)	0.0050 (5)	0.0022 (5)	−0.0014 (5)
C11	0.0218 (6)	0.0167 (6)	0.0182 (6)	0.0010 (5)	0.0018 (5)	−0.0027 (5)
C12	0.0183 (6)	0.0181 (6)	0.0174 (6)	0.0001 (5)	0.0038 (5)	0.0001 (5)
C13	0.0230 (7)	0.0294 (8)	0.0216 (7)	0.0033 (6)	0.0062 (6)	−0.0045 (6)
C14	0.0231 (7)	0.0208 (7)	0.0241 (7)	0.0059 (5)	0.0004 (6)	−0.0032 (5)
C15	0.0229 (7)	0.0212 (6)	0.0157 (6)	0.0027 (5)	0.0025 (5)	−0.0020 (5)

Cl1—C8	1.7176 (14)	C4—C5	1.432 (2)
Cl2—C12	1.7249 (14)	C5—C14	1.4926 (19)
F1—C15	1.3277 (18)	C7—C8	1.3946 (19)
F2—C15	1.3227 (18)	C7—C12	1.3971 (19)
F3—C15	1.3288 (17)	C8—C9	1.3890 (19)
O1—C6	1.3375 (17)	C9—C10	1.386 (2)
O1—C1	1.4233 (17)	C9—H9A	0.9500
O2—C1	1.2053 (18)	C10—C11	1.390 (2)
N1—C5	1.3238 (18)	C10—C15	1.5023 (19)
N1—N2	1.3967 (16)	C11—C12	1.3858 (19)
N2—C6	1.3436 (18)	C11—H11A	0.9500
N2—C7	1.4170 (17)	C13—H13A	0.9800
C1—C2	1.448 (2)	C13—H13B	0.9800
C2—C3	1.363 (2)	C13—H13C	0.9800
C2—H2A	0.9500	C14—H14A	0.9800
C3—C4	1.436 (2)	C14—H14B	0.9800
C3—C13	1.496 (2)	C14—H14C	0.9800
C4—C6	1.3749 (18)
C6—O1—C1	116.71 (11)	C10—C9—H9A	120.6
C5—N1—N2	105.51 (12)	C8—C9—H9A	120.6
C6—N2—N1	110.08 (11)	C9—C10—C11	122.04 (13)
C6—N2—C7	129.89 (12)	C9—C10—C15	119.89 (13)
N1—N2—C7	118.62 (11)	C11—C10—C15	118.07 (13)
O2—C1—O1	115.10 (13)	C12—C11—C10	118.21 (13)
O2—C1—C2	127.79 (14)	C12—C11—H11A	120.9
O1—C1—C2	117.11 (12)	C10—C11—H11A	120.9
C3—C2—C1	124.11 (13)	C11—C12—C7	121.19 (13)
C3—C2—H2A	117.9	C11—C12—Cl2	119.14 (11)
C1—C2—H2A	117.9	C7—C12—Cl2	119.64 (11)
C2—C3—C4	116.84 (13)	C3—C13—H13A	109.5
C2—C3—C13	122.77 (14)	C3—C13—H13B	109.5
C4—C3—C13	120.39 (13)	H13A—C13—H13B	109.5
C6—C4—C5	104.03 (12)	C3—C13—H13C	109.5
C6—C4—C3	117.46 (13)	H13A—C13—H13C	109.5
C5—C4—C3	138.49 (13)	H13B—C13—H13C	109.5
N1—C5—C4	111.20 (12)	C5—C14—H14A	109.5
N1—C5—C14	119.61 (13)	C5—C14—H14B	109.5
C4—C5—C14	129.18 (13)	H14A—C14—H14B	109.5
O1—C6—N2	123.12 (12)	C5—C14—H14C	109.5
O1—C6—C4	127.72 (13)	H14A—C14—H14C	109.5
N2—C6—C4	109.15 (12)	H14B—C14—H14C	109.5
C8—C7—C12	119.05 (12)	F2—C15—F1	107.52 (13)
C8—C7—N2	120.43 (12)	F2—C15—F3	106.52 (13)
C12—C7—N2	120.40 (12)	F1—C15—F3	106.16 (13)
C9—C8—C7	120.59 (13)	F2—C15—C10	112.43 (12)
C9—C8—Cl1	119.59 (11)	F1—C15—C10	112.49 (12)
C7—C8—Cl1	119.82 (11)	F3—C15—C10	111.32 (12)
C10—C9—C8	118.81 (13)
C5—N1—N2—C6	−1.53 (16)	C3—C4—C6—N2	−178.89 (12)
C5—N1—N2—C7	−169.29 (12)	C6—N2—C7—C8	122.18 (17)
C6—O1—C1—O2	179.89 (13)	N1—N2—C7—C8	−72.87 (17)
C6—O1—C1—C2	0.64 (18)	C6—N2—C7—C12	−62.0 (2)
O2—C1—C2—C3	−177.74 (15)	N1—N2—C7—C12	102.97 (16)
O1—C1—C2—C3	1.4 (2)	C12—C7—C8—C9	−3.5 (2)
C1—C2—C3—C4	−1.7 (2)	N2—C7—C8—C9	172.37 (13)
C1—C2—C3—C13	178.78 (14)	C12—C7—C8—Cl1	175.99 (11)
C2—C3—C4—C6	−0.07 (19)	N2—C7—C8—Cl1	−8.11 (19)
C13—C3—C4—C6	179.51 (13)	C7—C8—C9—C10	1.3 (2)
C2—C3—C4—C5	−178.26 (16)	Cl1—C8—C9—C10	−178.27 (11)
C13—C3—C4—C5	1.3 (3)	C8—C9—C10—C11	2.0 (2)
N2—N1—C5—C4	1.45 (16)	C8—C9—C10—C15	−178.05 (13)
N2—N1—C5—C14	−177.79 (12)	C9—C10—C11—C12	−2.9 (2)
C6—C4—C5—N1	−0.87 (16)	C15—C10—C11—C12	177.19 (13)
C3—C4—C5—N1	177.48 (16)	C10—C11—C12—C7	0.5 (2)
C6—C4—C5—C14	178.29 (14)	C10—C11—C12—Cl2	−177.47 (11)
C3—C4—C5—C14	−3.4 (3)	C8—C7—C12—C11	2.6 (2)
C1—O1—C6—N2	178.79 (13)	N2—C7—C12—C11	−173.26 (13)
C1—O1—C6—C4	−2.6 (2)	C8—C7—C12—Cl2	−179.39 (11)
N1—N2—C6—O1	179.89 (12)	N2—C7—C12—Cl2	4.71 (19)
C7—N2—C6—O1	−14.2 (2)	C9—C10—C15—F2	133.24 (15)
N1—N2—C6—C4	1.02 (16)	C11—C10—C15—F2	−46.84 (18)
C7—N2—C6—C4	166.98 (14)	C9—C10—C15—F1	11.7 (2)
C5—C4—C6—O1	−178.93 (14)	C11—C10—C15—F1	−168.40 (14)
C3—C4—C6—O1	2.3 (2)	C9—C10—C15—F3	−107.33 (16)
C5—C4—C6—N2	−0.13 (15)	C11—C10—C15—F3	72.59 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2i	0.95	2.44	3.3405 (18)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2i	0.95	2.44	3.3405 (18)	157

Symmetry code: (i) .