1-[2,6-Dichloro-4-(trifluoro­meth­yl)phen­yl]-5-[(3,4-methyl­enedioxy­phen­yl)methyl­eneimino]-1H-pyrazole-3-carbonitrile

Zhong, P.; Zhang, X.-H.; Yang, Z.-P.; Xiao, H.-P.; Hu, M.-L.

doi:10.1107/S1600536805012262

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1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(3,4-methylenedioxyphenyl)methyleneimino]-1H-pyrazole-3-carbonitrile

P. Zhong, X.-H. Zhang, Z.-P. Yang, H.-P. Xiao and M.-L. Hu

In the title molecule, C₁₉H₉Cl₂F₃N₄O₂, all bond lengths and angles are normal. The dihedral angle between the pyrazole and attached benzene rings is 77.5 (2)°. The crystal packing is mainly stabilized by van der Waals forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012262/cv6475sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012262/cv6475Isup2.hkl Contains datablock I

CCDC reference: 271848

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.065
wR factor = 0.154
Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for         C1

Author Response: see _publ_section_exptl_refinement


Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.389
            Value of mu given      =     0.384
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT213_ALERT_2_C Atom F21     has ADP max/min Ratio .............       3.70 prolat
PLAT213_ALERT_2_C Atom F1      has ADP max/min Ratio .............       3.50 prolat
PLAT213_ALERT_2_C Atom F2      has ADP max/min Ratio .............       3.10 prolat
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.09
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C11    ...       1.45 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  N3      ..       3.28 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O2      ..       3.07 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.17 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.60 Deg.
              F1   -C1   -F21     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.50 Deg.
              F2   -C1   -F23     1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.59
           From the CIF: _reflns_number_total               3274
           Count of symmetry unique reflns         1932
           Completeness (_total/calc)            169.46%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1342
           Fraction of Friedel pairs measured     0.695
           Are heavy atom types Z>Si present        yes

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

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

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(3,4- methylenedioxyphenyl)methyleneimino]-1H-pyrazole-3-carbonitrile top

Crystal data top

C₁₉H₉Cl₂F₃N₄O₂	F(000) = 452
M_r = 453.20	D_x = 1.547 Mg m⁻³
Monoclinic, P2₁	Melting point = 446–447 K
Hall symbol: P2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.4308 (11) Å	Cell parameters from 1189 reflections
b = 9.8948 (17) Å	θ = 2.5–24.2°
c = 15.356 (3) Å	µ = 0.38 mm⁻¹
β = 99.179 (4)°	T = 298 K
V = 964.6 (3) Å³	Block, colourless
Z = 2	0.21 × 0.19 × 0.13 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	3274 independent reflections
Radiation source: fine-focus sealed tube	2530 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 25.6°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
T_min = 0.924, T_max = 0.952	k = −12→11
5177 measured reflections	l = −18→13

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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0709P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3274 reflections	Δρ_max = 0.24 e Å⁻³
308 parameters	Δρ_min = −0.22 e Å⁻³
31 restraints	Absolute structure: Flack (1983), with how many Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.15 (11)

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	Occ. (<1)
C1	0.0697 (9)	−0.0108 (5)	0.0559 (4)	0.0679 (19)
F1	0.102 (6)	−0.1353 (10)	0.0752 (12)	0.161 (16)	0.45 (3)
F2	0.250 (3)	0.042 (3)	0.0548 (19)	0.19 (2)	0.45 (3)
F3	−0.027 (3)	−0.008 (3)	−0.0235 (6)	0.133 (13)	0.45 (3)
F21	−0.014 (2)	−0.1225 (12)	0.0274 (15)	0.170 (15)	0.55 (3)
F22	0.084 (3)	0.0607 (16)	−0.0122 (9)	0.106 (7)	0.55 (3)
F23	0.2590 (13)	−0.038 (2)	0.0909 (7)	0.100 (7)	0.55 (3)
Cl1	−0.0852 (3)	0.0295 (2)	0.37516 (9)	0.0694 (5)
Cl2	−0.4769 (3)	0.3459 (2)	0.11530 (12)	0.0936 (7)
O1	0.6143 (6)	0.8124 (5)	0.2177 (3)	0.0753 (13)
O2	0.4345 (6)	0.6494 (5)	0.1282 (2)	0.0595 (10)
N1	−0.3554 (7)	0.2621 (5)	0.3028 (3)	0.0462 (11)
N2	−0.5176 (7)	0.2095 (5)	0.3381 (3)	0.0542 (12)
N3	−0.8479 (9)	0.2833 (7)	0.4894 (4)	0.0752 (16)
N4	−0.1302 (7)	0.4481 (4)	0.3011 (3)	0.0447 (11)
C2	−0.0510 (9)	0.0567 (6)	0.1208 (3)	0.0488 (14)
C3	−0.0155 (9)	0.0197 (6)	0.2078 (4)	0.0506 (14)
H3	0.0797	−0.0490	0.2269	0.044 (14)*
C4	−0.1214 (9)	0.0830 (6)	0.2670 (3)	0.0462 (13)
C5	−0.2616 (8)	0.1883 (6)	0.2399 (3)	0.0457 (13)
C6	−0.2980 (9)	0.2188 (6)	0.1513 (4)	0.0562 (15)
C7	−0.1968 (9)	0.1554 (6)	0.0924 (3)	0.0525 (14)
H7	−0.2251	0.1787	0.0330	0.047 (14)*
C8	−0.2934 (8)	0.3853 (5)	0.3355 (3)	0.0413 (12)
C9	−0.4185 (8)	0.4183 (6)	0.3965 (3)	0.0451 (13)
H9	−0.4149	0.4964	0.4303	0.09 (2)*
C10	−0.5527 (8)	0.3078 (6)	0.3953 (3)	0.0457 (13)
C11	−0.7204 (9)	0.2900 (6)	0.4473 (4)	0.0534 (15)
C12	−0.0373 (8)	0.5482 (6)	0.3435 (3)	0.0465 (13)
H12	−0.0764	0.5741	0.3968	0.042 (14)*
C13	0.1311 (7)	0.6217 (5)	0.3112 (3)	0.0392 (12)
C14	0.2372 (8)	0.7231 (6)	0.3636 (4)	0.0509 (14)
H14	0.1943	0.7441	0.4170	0.031 (13)*
C15	0.4027 (9)	0.7944 (7)	0.3380 (4)	0.0588 (16)
H15	0.4722	0.8629	0.3725	0.053 (16)*
C16	0.4581 (8)	0.7578 (6)	0.2592 (4)	0.0521 (15)
C17	0.3532 (8)	0.6597 (6)	0.2053 (3)	0.0459 (13)
C18	0.1902 (8)	0.5892 (6)	0.2305 (4)	0.0459 (13)
H18	0.1194	0.5230	0.1943	0.09 (2)*
C19	0.6191 (10)	0.7345 (8)	0.1426 (5)	0.074 (2)
H19A	0.7456	0.6796	0.1506	0.042 (14)*
H19B	0.6211	0.7924	0.0918	0.08 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.090 (5)	0.063 (5)	0.058 (4)	0.018 (4)	0.035 (4)	0.003 (4)
F1	0.33 (4)	0.082 (16)	0.095 (12)	0.12 (2)	0.114 (17)	0.036 (11)
F2	0.16 (3)	0.19 (3)	0.27 (5)	−0.08 (2)	0.17 (3)	−0.10 (3)
F3	0.124 (16)	0.22 (3)	0.053 (8)	0.065 (17)	0.021 (7)	−0.022 (11)
F21	0.223 (19)	0.113 (17)	0.22 (3)	−0.076 (14)	0.16 (2)	−0.121 (17)
F22	0.133 (14)	0.122 (11)	0.082 (9)	0.055 (10)	0.078 (8)	0.035 (8)
F23	0.085 (10)	0.128 (17)	0.095 (7)	0.043 (9)	0.040 (7)	0.023 (8)
Cl1	0.1005 (12)	0.0657 (11)	0.0431 (8)	0.0073 (9)	0.0148 (8)	0.0039 (7)
Cl2	0.1302 (15)	0.0872 (15)	0.0681 (11)	0.0598 (13)	0.0302 (10)	0.0133 (9)
O1	0.067 (3)	0.086 (4)	0.079 (3)	−0.029 (3)	0.027 (2)	−0.005 (3)
O2	0.063 (2)	0.060 (3)	0.061 (2)	−0.001 (2)	0.027 (2)	0.001 (2)
N1	0.063 (3)	0.037 (3)	0.045 (3)	−0.007 (2)	0.031 (2)	−0.002 (2)
N2	0.064 (3)	0.047 (3)	0.056 (3)	−0.008 (2)	0.025 (2)	−0.006 (2)
N3	0.075 (3)	0.093 (4)	0.066 (3)	−0.021 (3)	0.036 (3)	−0.017 (3)
N4	0.054 (3)	0.036 (3)	0.048 (3)	−0.007 (2)	0.020 (2)	−0.004 (2)
C2	0.059 (3)	0.043 (4)	0.047 (3)	−0.001 (3)	0.019 (3)	0.002 (3)
C3	0.062 (3)	0.035 (3)	0.056 (3)	0.005 (3)	0.015 (3)	0.000 (3)
C4	0.058 (3)	0.038 (3)	0.046 (3)	−0.013 (3)	0.018 (3)	−0.004 (2)
C5	0.058 (3)	0.036 (3)	0.047 (3)	−0.014 (3)	0.022 (3)	−0.002 (2)
C6	0.071 (4)	0.044 (4)	0.058 (4)	0.012 (3)	0.023 (3)	0.007 (3)
C7	0.078 (4)	0.051 (4)	0.035 (3)	0.005 (3)	0.028 (3)	0.010 (3)
C8	0.053 (3)	0.030 (3)	0.044 (3)	−0.007 (2)	0.017 (2)	0.001 (2)
C9	0.050 (3)	0.037 (3)	0.050 (3)	−0.006 (3)	0.014 (2)	−0.004 (3)
C10	0.053 (3)	0.049 (4)	0.038 (3)	0.001 (3)	0.019 (2)	−0.002 (3)
C11	0.061 (3)	0.050 (4)	0.054 (4)	−0.015 (3)	0.024 (3)	−0.008 (3)
C12	0.056 (3)	0.047 (4)	0.041 (3)	0.005 (3)	0.022 (2)	0.000 (3)
C13	0.039 (3)	0.039 (3)	0.042 (3)	0.001 (2)	0.012 (2)	0.001 (2)
C14	0.051 (3)	0.052 (4)	0.051 (3)	−0.002 (3)	0.016 (3)	−0.009 (3)
C15	0.063 (4)	0.056 (4)	0.057 (4)	−0.015 (3)	0.008 (3)	−0.010 (3)
C16	0.045 (3)	0.049 (4)	0.061 (4)	−0.010 (3)	0.004 (3)	0.007 (3)
C17	0.049 (3)	0.046 (4)	0.045 (3)	0.007 (3)	0.015 (3)	0.006 (3)
C18	0.045 (3)	0.040 (3)	0.053 (3)	−0.003 (3)	0.006 (3)	0.001 (3)
C19	0.052 (4)	0.101 (6)	0.076 (5)	−0.004 (4)	0.029 (3)	0.011 (4)

Geometric parameters (Å, º) top

C1—F2	1.275 (6)	C2—C3	1.368 (8)
C1—F1	1.276 (6)	C2—C7	1.376 (7)
C1—F21	1.277 (6)	C3—C4	1.371 (8)
C1—F3	1.278 (6)	C3—H3	0.9304
C1—F22	1.279 (6)	C4—C5	1.397 (8)
C1—F23	1.279 (6)	C5—C6	1.376 (8)
C1—C2	1.512 (8)	C6—C7	1.350 (8)
F1—F21	0.968 (18)	C7—H7	0.9302
F1—F23	1.39 (2)	C8—C9	1.368 (7)
F2—F23	0.97 (2)	C9—C10	1.391 (8)
F2—F22	1.370 (18)	C9—H9	0.9291
F3—F22	0.983 (16)	C10—C11	1.451 (7)
F3—F21	1.373 (13)	C12—C13	1.455 (7)
Cl1—C4	1.723 (6)	C12—H12	0.9298
Cl2—C6	1.734 (6)	C13—C18	1.390 (7)
O1—C16	1.382 (7)	C13—C14	1.395 (7)
O1—C19	1.391 (8)	C14—C15	1.384 (8)
O2—C17	1.373 (6)	C14—H14	0.9295
O2—C19	1.444 (7)	C15—C16	1.365 (8)
N1—C8	1.354 (7)	C15—H15	0.9297
N1—N2	1.354 (6)	C16—C17	1.379 (8)
N1—C5	1.421 (7)	C17—C18	1.366 (7)
N2—C10	1.354 (7)	C18—H18	0.9299
N3—C11	1.124 (7)	C19—H19A	0.9696
N4—C12	1.279 (6)	C19—H19B	0.9696
N4—C8	1.394 (6)

F2—C1—F1	106.6 (5)	C4—C3—H3	119.7
F2—C1—F21	133.4 (12)	C3—C4—C5	120.5 (5)
F1—C1—F21	44.6 (8)	C3—C4—Cl1	119.6 (5)
F2—C1—F3	106.5 (5)	C5—C4—Cl1	119.9 (4)
F1—C1—F3	106.2 (5)	C6—C5—C4	117.3 (5)
F21—C1—F3	65.0 (7)	C6—C5—N1	122.4 (5)
F2—C1—F22	64.9 (9)	C4—C5—N1	120.3 (5)
F1—C1—F22	133.8 (11)	C7—C6—C5	122.4 (5)
F21—C1—F22	106.3 (5)	C7—C6—Cl2	119.3 (5)
F3—C1—F22	45.2 (7)	C5—C6—Cl2	118.3 (5)
F2—C1—F23	44.5 (11)	C6—C7—C2	119.6 (5)
F1—C1—F23	65.7 (10)	C6—C7—H7	120.1
F21—C1—F23	106.3 (5)	C2—C7—H7	120.3
F3—C1—F23	133.7 (10)	N1—C8—C9	107.3 (5)
F22—C1—F23	105.8 (5)	N1—C8—N4	117.1 (4)
F2—C1—C2	113.0 (9)	C9—C8—N4	135.5 (5)
F1—C1—C2	110.8 (9)	C8—C9—C10	103.6 (5)
F21—C1—C2	112.0 (7)	C8—C9—H9	128.0
F3—C1—C2	113.3 (8)	C10—C9—H9	128.4
F22—C1—C2	114.1 (7)	N2—C10—C9	114.0 (5)
F23—C1—C2	111.9 (7)	N2—C10—C11	119.0 (5)
F21—F1—C1	67.8 (5)	C9—C10—C11	127.0 (5)
F21—F1—F23	119.7 (9)	N3—C11—C10	176.1 (7)
C1—F1—F23	57.3 (6)	N4—C12—C13	121.7 (5)
F23—F2—C1	68.0 (6)	N4—C12—H12	119.4
F23—F2—F22	120.6 (8)	C13—C12—H12	118.8
C1—F2—F22	57.7 (5)	C18—C13—C14	120.2 (5)
F22—F3—C1	67.4 (5)	C18—C13—C12	120.8 (5)
F22—F3—F21	119.6 (8)	C14—C13—C12	119.0 (5)
C1—F3—F21	57.5 (4)	C15—C14—C13	122.0 (5)
F1—F21—C1	67.7 (5)	C15—C14—H14	119.1
F1—F21—F3	120.5 (8)	C13—C14—H14	118.9
C1—F21—F3	57.5 (4)	C16—C15—C14	115.9 (5)
F3—F22—C1	67.4 (4)	C16—C15—H15	122.0
F3—F22—F2	119.9 (9)	C14—C15—H15	122.1
C1—F22—F2	57.4 (5)	C15—C16—C17	123.1 (5)
F2—F23—C1	67.5 (6)	C15—C16—O1	128.1 (5)
F2—F23—F1	119.7 (8)	C17—C16—O1	108.7 (5)
C1—F23—F1	57.1 (5)	C18—C17—O2	128.4 (5)
C16—O1—C19	106.2 (5)	C18—C17—C16	120.9 (5)
C17—O2—C19	103.9 (5)	O2—C17—C16	110.6 (5)
C8—N1—N2	113.5 (4)	C17—C18—C13	117.7 (5)
C8—N1—C5	125.7 (4)	C17—C18—H18	121.0
N2—N1—C5	120.8 (4)	C13—C18—H18	121.2
C10—N2—N1	101.7 (4)	O1—C19—O2	108.9 (5)
C12—N4—C8	118.1 (4)	O1—C19—H19A	109.5
C3—C2—C7	119.9 (5)	O2—C19—H19A	110.2
C3—C2—C1	120.1 (5)	O1—C19—H19B	110.2
C7—C2—C1	119.9 (5)	O2—C19—H19B	109.7
C2—C3—C4	120.2 (5)	H19A—C19—H19B	108.3
C2—C3—H3	120.1

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