4-Difluoro­methyl-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one

Heng, J.; Zhu, H.-J.; Tang, Q.-G.; Yan, H.-L.

doi:10.1107/S1600536806019003

4-Difluoromethyl-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one

J. Heng, H.-J. Zhu, Q.-G. Tang and H.-L. Yan

In the crystal structure of the title compound, C₁₀H₉F₂N₃O, a derivative of triazolinone, there are intramolecular C—H

O and C—H

N and intermolecular C—H

F and C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019003/jh2013sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019003/jh2013Isup2.hkl Contains datablock I

CCDC reference: 613743

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.043
wR factor = 0.121
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXS97.

4-Difluoromethyl-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one top

Crystal data top

C₁₀H₉F₂N₃O	Z = 2
M_r = 225.20	F(000) = 232
Triclinic, P1	D_x = 1.445 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2910 (15) Å	Cell parameters from 25 reflections
b = 8.2100 (16) Å	θ = 11–14°
c = 8.8710 (18) Å	µ = 0.12 mm⁻¹
α = 85.88 (3)°	T = 293 K
β = 80.43 (3)°	Block, colourless
γ = 81.71 (3)°	0.30 × 0.20 × 0.10 mm
V = 517.53 (19) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1422 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.013
Graphite monochromator	θ_max = 26.0°, θ_min = 2.3°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
T_min = 0.964, T_max = 0.988	l = −10→10
2188 measured reflections	3 standard reflections every 200 reflections
2019 independent reflections	intensity decay: none

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.06P)² + 0.06P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2019 reflections	Δρ_max = 0.17 e Å⁻³
146 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.131 (13)

Special details top

Experimental. ¹H NMR (CDCl₃): δ 8.05–8.08 (m, 2H), 7.59–7.64 (m, 2H), 7.41–7.45 (m, 2H), 2.69 (s, 3H).

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
F1	0.3603 (2)	0.70240 (19)	1.03226 (14)	0.0951 (5)
F2	0.0949 (2)	0.62729 (16)	1.01687 (15)	0.0940 (5)
O	0.1464 (2)	1.06459 (16)	0.81753 (15)	0.0699 (4)
N1	0.2319 (2)	0.77975 (17)	0.81876 (16)	0.0526 (4)
N2	0.2493 (2)	0.91199 (17)	0.59845 (16)	0.0506 (4)
N3	0.3106 (2)	0.74604 (19)	0.57154 (18)	0.0578 (4)
C1	0.3126 (3)	1.0936 (3)	0.2050 (3)	0.0800 (7)
H1A	0.3591	1.0595	0.1066	0.096*
C2	0.3159 (3)	0.9807 (3)	0.3270 (2)	0.0671 (6)
H2A	0.3652	0.8713	0.3110	0.081*
C3	0.2462 (2)	1.0300 (2)	0.4730 (2)	0.0517 (5)
C4	0.1735 (3)	1.1920 (2)	0.4960 (2)	0.0680 (6)
H4A	0.1255	1.2264	0.5941	0.082*
C5	0.1727 (3)	1.3033 (3)	0.3713 (3)	0.0802 (7)
H5A	0.1240	1.4130	0.3864	0.096*
C6	0.2422 (3)	1.2550 (3)	0.2261 (3)	0.0756 (6)
H6A	0.2415	1.3309	0.1431	0.091*
C7	0.3502 (4)	0.4907 (2)	0.7326 (3)	0.0800 (7)
H7A	0.3932	0.4398	0.6366	0.120*
H7B	0.2422	0.4442	0.7849	0.120*
H7C	0.4482	0.4716	0.7944	0.120*
C8	0.2993 (3)	0.6709 (2)	0.7044 (2)	0.0549 (5)
C9	0.2008 (2)	0.9374 (2)	0.7510 (2)	0.0523 (5)
C10	0.1977 (3)	0.7519 (2)	0.9793 (2)	0.0632 (5)
H10A	0.1331	0.8523	1.0282	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0925 (10)	0.1221 (12)	0.0682 (8)	0.0056 (8)	−0.0272 (7)	0.0051 (7)
F2	0.1118 (12)	0.0779 (9)	0.0878 (9)	−0.0315 (8)	0.0053 (8)	0.0140 (7)
O	0.0900 (11)	0.0501 (8)	0.0625 (9)	−0.0006 (7)	0.0038 (7)	−0.0094 (6)
N1	0.0555 (9)	0.0481 (9)	0.0522 (9)	−0.0022 (7)	−0.0063 (7)	−0.0029 (7)
N2	0.0526 (9)	0.0469 (8)	0.0507 (9)	−0.0013 (6)	−0.0073 (6)	−0.0049 (6)
N3	0.0605 (10)	0.0517 (9)	0.0602 (10)	0.0004 (7)	−0.0111 (7)	−0.0094 (7)
C1	0.0957 (18)	0.0901 (18)	0.0553 (13)	−0.0245 (14)	−0.0067 (11)	0.0007 (11)
C2	0.0787 (14)	0.0656 (13)	0.0572 (12)	−0.0134 (11)	−0.0068 (10)	−0.0051 (10)
C3	0.0432 (10)	0.0562 (11)	0.0571 (11)	−0.0099 (8)	−0.0110 (8)	0.0011 (8)
C4	0.0730 (14)	0.0601 (12)	0.0661 (13)	0.0002 (10)	−0.0062 (10)	0.0003 (10)
C5	0.0801 (16)	0.0640 (14)	0.0911 (18)	−0.0003 (11)	−0.0131 (13)	0.0127 (12)
C6	0.0775 (15)	0.0800 (16)	0.0705 (14)	−0.0191 (12)	−0.0188 (11)	0.0220 (12)
C7	0.1015 (18)	0.0522 (12)	0.0810 (15)	0.0067 (11)	−0.0136 (13)	−0.0046 (10)
C8	0.0524 (11)	0.0513 (10)	0.0603 (12)	−0.0009 (8)	−0.0102 (8)	−0.0065 (9)
C9	0.0491 (10)	0.0510 (10)	0.0554 (11)	−0.0055 (8)	−0.0044 (8)	−0.0034 (8)
C10	0.0690 (13)	0.0572 (12)	0.0589 (12)	−0.0040 (10)	−0.0039 (10)	0.0034 (9)

Geometric parameters (Å, º) top

F1—C10	1.346 (2)	C2—C3	1.377 (3)
F2—C10	1.345 (2)	C2—H2A	0.9300
O—C9	1.219 (2)	C3—C4	1.376 (3)
N1—C8	1.381 (2)	C4—C5	1.383 (3)
N1—C9	1.392 (2)	C4—H4A	0.9300
N1—C10	1.412 (2)	C5—C6	1.368 (3)
N2—C9	1.364 (2)	C5—H5A	0.9300
N2—N3	1.396 (2)	C6—H6A	0.9300
N2—C3	1.423 (2)	C7—C8	1.486 (3)
N3—C8	1.286 (2)	C7—H7A	0.9600
C1—C6	1.364 (3)	C7—H7B	0.9600
C1—C2	1.374 (3)	C7—H7C	0.9600
C1—H1A	0.9300	C10—H10A	0.9800

C8—N1—C9	108.30 (15)	C1—C6—C5	118.9 (2)
C8—N1—C10	130.39 (16)	C1—C6—H6A	120.6
C9—N1—C10	121.29 (15)	C5—C6—H6A	120.6
C9—N2—N3	111.71 (14)	C8—C7—H7A	109.5
C9—N2—C3	128.48 (15)	C8—C7—H7B	109.5
N3—N2—C3	119.80 (14)	H7A—C7—H7B	109.5
C8—N3—N2	105.67 (14)	C8—C7—H7C	109.5
C6—C1—C2	121.0 (2)	H7A—C7—H7C	109.5
C6—C1—H1A	119.5	H7B—C7—H7C	109.5
C2—C1—H1A	119.5	N3—C8—N1	111.07 (16)
C1—C2—C3	119.9 (2)	N3—C8—C7	124.93 (18)
C1—C2—H2A	120.1	N1—C8—C7	124.00 (18)
C3—C2—H2A	120.1	O—C9—N2	130.43 (17)
C4—C3—C2	119.81 (18)	O—C9—N1	126.32 (17)
C4—C3—N2	120.75 (17)	N2—C9—N1	103.24 (15)
C2—C3—N2	119.43 (17)	F2—C10—F1	105.52 (16)
C3—C4—C5	119.1 (2)	F2—C10—N1	110.18 (17)
C3—C4—H4A	120.4	F1—C10—N1	110.13 (16)
C5—C4—H4A	120.4	F2—C10—H10A	110.3
C6—C5—C4	121.3 (2)	F1—C10—H10A	110.3
C6—C5—H5A	119.4	N1—C10—H10A	110.3
C4—C5—H5A	119.4

C9—N2—N3—C8	0.3 (2)	C9—N1—C8—N3	−0.9 (2)
C3—N2—N3—C8	179.51 (15)	C10—N1—C8—N3	−179.83 (17)
C6—C1—C2—C3	0.5 (3)	C9—N1—C8—C7	179.55 (19)
C1—C2—C3—C4	0.0 (3)	C10—N1—C8—C7	0.6 (3)
C1—C2—C3—N2	179.67 (18)	N3—N2—C9—O	177.90 (18)
C9—N2—C3—C4	−5.7 (3)	C3—N2—C9—O	−1.2 (3)
N3—N2—C3—C4	175.19 (16)	N3—N2—C9—N1	−0.80 (18)
C9—N2—C3—C2	174.60 (17)	C3—N2—C9—N1	−179.93 (15)
N3—N2—C3—C2	−4.5 (2)	C8—N1—C9—O	−177.78 (18)
C2—C3—C4—C5	−0.3 (3)	C10—N1—C9—O	1.3 (3)
N2—C3—C4—C5	−179.98 (18)	C8—N1—C9—N2	0.99 (18)
C3—C4—C5—C6	0.2 (3)	C10—N1—C9—N2	−179.96 (15)
C2—C1—C6—C5	−0.6 (4)	C8—N1—C10—F2	−50.0 (3)
C4—C5—C6—C1	0.3 (4)	C9—N1—C10—F2	131.18 (18)
N2—N3—C8—N1	0.4 (2)	C8—N1—C10—F1	66.0 (3)
N2—N3—C8—C7	179.93 (18)	C9—N1—C10—F1	−112.82 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N3	0.93	2.46	2.795 (3)	102
C4—H4A···O	0.93	2.32	2.952 (2)	125
C7—H7C···F1ⁱ	0.96	2.49	3.368 (3)	153
C10—H10A···O	0.98	2.46	2.857 (2)	104
C10—H10A···Oⁱⁱ	0.98	2.30	3.100 (2)	138

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+2, −z+2.

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4-Difluoro­methyl-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one

Supporting information

Key indicators

checkCIF/PLATON results

4-Difluoromethyl-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one