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Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026256/tk2157sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026256/tk2157Isup2.hkl |
CCDC reference: 617733
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.006 Å - R factor = 0.058
- wR factor = 0.186
- Data-to-parameter ratio = 18.1
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.006 ÅcheckCIF/PLATON results
No syntax errors found
Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C1
Alert level A
| Author Response: see _publ_section_exptl_refinement |
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _diffrn_reflns_theta_full 28.30 From the CIF: _reflns_number_total 4736 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4991 Completeness (_total/calc) 94.89% PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT213_ALERT_2_C Atom F3 has ADP max/min Ratio ............. 3.30 prola PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C9 ... 1.43 Ang.
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Alert level B
Alert level C
According to the method of Zhong et al. (2005), using 5-amino- 3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole (2.5 mmol), followed by reaction with 4-chlorobenzaldehyde (2.5 mmol) and HCl (2 ml) in anhydrous ethanol (5 ml), we obtained 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-cyano- 5-[(4-chlorobenzylidene)amino]-1H-pyrazole, which was then reacted with N-bromosuccinimide (1.5 mmol) (Philippe, 2000) in acetonitrile (6 ml) at room temperature. After being stirred a few minutes, the reaction was monitored by TLC until the starting materials were consumed. Finally, the reaction mixture was evaporated under reduced pressure to provide the required crude product, which was then partitioned between dichloromethane and water, separating and drying the organic phase and evaporating it under reduced pressure gave the title compound in 90.8% yield. Colorless single crystals suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol-acetone (2:1) solution of (I), m.p. 488–489 K. IR (KBr, ν cm-1): 3047, 2202, 1618, 1387, 1313, 1179, 1136, 825; 1H NMR (C3D6O, δ, p.p.m.): 9.39 (s, 1H), 8.14 (s, 2H), 7.90 (d, J = 8.52 Hz, 2H), 7.55 (d, J = 8.52 Hz, 2H); 13C NMR (C3D6O, δ, p.p.m.): 167.4, 148.4, 140.2, 137.6, 136.4, 134.5 (q, J = 34.1 Hz), 134.3, 131.9, 130.2 (2 C), 130.1 (2 C), 127.2 (2 C), 127.1 (2 C), 121.5 (q, J = 271.1 Hz), 112.4.
All H atoms were constrained to ride on their parent atoms, with C—H = 0.93 Å, and with Uiso(H) = 1.2eq(C). The low Ueq of C1 as compared to its neighbours may be attributed to the high displacement parameters for atoms F1, F2 and F3, indicating either large thermal motion or rotational disorder of the trifluoromethyl group. However, attempts to represent the CF3 group using a disorder model were unsuccessful. The maximum residual electron density peak was located 1.27 Å from the C1 and F1 atoms.
The title compound, (I), (Fig. 1) is similar to the very effective insecticides used to treat animals such as cows and sheep (Philippe, 1997, 2000) and its structure is reported here. The molecule of (I) contains three essentially planar rings. The dihedral angles between the central pyrazole ring (C9—C11, N1, N2) and the benzene (C2—C7) and (C13—C16) ring planes are 84.3 (2)° and 68.5 (2)°, respectively.
For related literature, see: Philippe (1997, 2000); Zhong et al. (2005).
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.
![[Figure 1]](http://journals.iucr.org/e/issues/2007/07/00/tk2157/tk2157fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing the atom numbering scheme and displacement ellipsoids at 50% probability level. |
| C18H7BrCl3F3N4 | Dx = 1.731 Mg m−3 |
| Mr = 522.54 | Melting point = 488–489 K |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 4261 reflections |
| a = 10.0338 (7) Å | θ = 2.4–21.3° |
| b = 11.5819 (8) Å | µ = 2.49 mm−1 |
| c = 34.499 (3) Å | T = 298 K |
| V = 4009.1 (5) Å3 | Block, colorless |
| Z = 8 | 0.39 × 0.17 × 0.16 mm |
| F(000) = 2048 |
| Bruker APEX area-detector diffractometer | 4736 independent reflections |
| Radiation source: fine-focus sealed tube | 3014 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.036 |
| φ and ω scans | θmax = 28.3°, θmin = 1.2° |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −13→9 |
| Tmin = 0.444, Tmax = 0.691 | k = −15→14 |
| 23679 measured reflections | l = −45→45 |
| 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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.186 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0966P)2 + 3.5182P] where P = (Fo2 + 2Fc2)/3 |
| 4736 reflections | (Δ/σ)max = 0.001 |
| 262 parameters | Δρmax = 1.20 e Å−3 |
| 0 restraints | Δρmin = −0.84 e Å−3 |
| C18H7BrCl3F3N4 | V = 4009.1 (5) Å3 |
| Mr = 522.54 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 10.0338 (7) Å | µ = 2.49 mm−1 |
| b = 11.5819 (8) Å | T = 298 K |
| c = 34.499 (3) Å | 0.39 × 0.17 × 0.16 mm |
| Bruker APEX area-detector diffractometer | 4736 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | 3014 reflections with I > 2σ(I) |
| Tmin = 0.444, Tmax = 0.691 | Rint = 0.036 |
| 23679 measured reflections |
| R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
| wR(F2) = 0.186 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 1.20 e Å−3 |
| 4736 reflections | Δρmin = −0.84 e Å−3 |
| 262 parameters |
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 | ||
| Br1 | 1.01932 (6) | 0.22489 (5) | 0.020072 (16) | 0.0781 (2) | |
| Cl1 | 0.50245 (14) | 0.43701 (13) | 0.08080 (3) | 0.0729 (4) | |
| Cl2 | 0.81344 (15) | 0.17122 (15) | 0.17059 (4) | 0.0894 (5) | |
| Cl3 | 1.32776 (14) | 0.77979 (12) | 0.17945 (4) | 0.0804 (4) | |
| F1 | 0.4269 (6) | 0.3602 (5) | 0.25418 (13) | 0.150 (2) | |
| F2 | 0.3552 (4) | 0.4993 (4) | 0.22440 (9) | 0.1293 (18) | |
| F3 | 0.5420 (6) | 0.5033 (7) | 0.25062 (15) | 0.200 (4) | |
| N1 | 0.7224 (3) | 0.2693 (3) | 0.09621 (9) | 0.0474 (8) | |
| N2 | 0.6684 (3) | 0.1819 (3) | 0.07601 (10) | 0.0530 (8) | |
| N3 | 0.7249 (5) | −0.0086 (4) | 0.00155 (12) | 0.0825 (14) | |
| N4 | 0.9101 (3) | 0.3884 (3) | 0.10357 (9) | 0.0471 (8) | |
| C1 | 0.4628 (5) | 0.4421 (5) | 0.23040 (13) | 0.0639 (13) | |
| C2 | 0.5282 (4) | 0.3954 (4) | 0.19469 (12) | 0.0484 (9) | |
| C3 | 0.4871 (4) | 0.4337 (4) | 0.15874 (12) | 0.0474 (9) | |
| H3 | 0.4178 | 0.4867 | 0.1564 | 0.057* | |
| C4 | 0.5516 (4) | 0.3913 (3) | 0.12611 (11) | 0.0443 (9) | |
| C5 | 0.6547 (4) | 0.3127 (3) | 0.12953 (11) | 0.0438 (9) | |
| C6 | 0.6911 (4) | 0.2741 (4) | 0.16625 (13) | 0.0527 (10) | |
| C7 | 0.6291 (4) | 0.3172 (4) | 0.19877 (12) | 0.0552 (10) | |
| H7 | 0.6557 | 0.2934 | 0.2233 | 0.066* | |
| C8 | 0.7399 (5) | 0.0671 (4) | 0.02214 (12) | 0.0581 (11) | |
| C9 | 0.7597 (4) | 0.1600 (3) | 0.04885 (11) | 0.0474 (9) | |
| C10 | 0.8695 (4) | 0.2339 (3) | 0.05139 (11) | 0.0475 (9) | |
| C11 | 0.8445 (4) | 0.3047 (3) | 0.08248 (11) | 0.0446 (9) | |
| C12 | 0.9998 (4) | 0.4510 (4) | 0.08793 (12) | 0.0483 (9) | |
| H12 | 1.0163 | 0.4440 | 0.0615 | 0.058* | |
| C13 | 1.0769 (4) | 0.5334 (3) | 0.11074 (11) | 0.0425 (8) | |
| C14 | 1.1751 (5) | 0.5990 (4) | 0.09282 (13) | 0.0585 (11) | |
| H14 | 1.1897 | 0.5908 | 0.0663 | 0.070* | |
| C15 | 1.2515 (5) | 0.6764 (4) | 0.11383 (14) | 0.0642 (12) | |
| H15 | 1.3170 | 0.7203 | 0.1017 | 0.077* | |
| C16 | 1.2289 (4) | 0.6867 (3) | 0.15246 (12) | 0.0501 (9) | |
| C17 | 1.1317 (4) | 0.6240 (3) | 0.17108 (12) | 0.0503 (9) | |
| H17 | 1.1176 | 0.6331 | 0.1975 | 0.060* | |
| C18 | 1.0557 (4) | 0.5480 (3) | 0.15006 (11) | 0.0468 (9) | |
| H18 | 0.9892 | 0.5058 | 0.1624 | 0.056* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.0779 (4) | 0.0866 (4) | 0.0696 (4) | −0.0145 (3) | 0.0327 (3) | −0.0231 (3) |
| Cl1 | 0.0865 (9) | 0.0873 (9) | 0.0450 (6) | 0.0215 (7) | 0.0038 (5) | 0.0120 (6) |
| Cl2 | 0.0807 (9) | 0.1045 (11) | 0.0831 (9) | 0.0444 (9) | −0.0068 (7) | 0.0048 (8) |
| Cl3 | 0.0756 (9) | 0.0734 (9) | 0.0922 (10) | −0.0251 (7) | −0.0067 (7) | −0.0206 (7) |
| F1 | 0.191 (5) | 0.163 (4) | 0.097 (3) | 0.050 (4) | 0.084 (3) | 0.037 (3) |
| F2 | 0.137 (4) | 0.185 (4) | 0.066 (2) | 0.092 (3) | 0.009 (2) | −0.021 (2) |
| F3 | 0.128 (4) | 0.342 (9) | 0.130 (4) | −0.077 (4) | 0.041 (3) | −0.163 (6) |
| N1 | 0.0422 (18) | 0.0493 (19) | 0.0507 (19) | −0.0050 (15) | 0.0045 (14) | −0.0097 (15) |
| N2 | 0.050 (2) | 0.0506 (19) | 0.058 (2) | −0.0075 (16) | −0.0029 (16) | −0.0093 (17) |
| N3 | 0.107 (4) | 0.076 (3) | 0.065 (3) | −0.003 (3) | −0.011 (2) | −0.028 (2) |
| N4 | 0.0471 (19) | 0.0453 (18) | 0.0487 (18) | −0.0064 (15) | 0.0043 (14) | −0.0071 (15) |
| C1 | 0.063 (3) | 0.087 (4) | 0.041 (2) | 0.003 (3) | 0.003 (2) | −0.011 (2) |
| C2 | 0.043 (2) | 0.056 (2) | 0.047 (2) | −0.0071 (18) | 0.0034 (16) | −0.0035 (18) |
| C3 | 0.043 (2) | 0.051 (2) | 0.049 (2) | 0.0034 (18) | 0.0023 (16) | 0.0014 (18) |
| C4 | 0.046 (2) | 0.048 (2) | 0.0394 (19) | −0.0045 (17) | −0.0002 (16) | 0.0034 (16) |
| C5 | 0.040 (2) | 0.044 (2) | 0.046 (2) | −0.0082 (17) | 0.0037 (16) | −0.0053 (17) |
| C6 | 0.043 (2) | 0.056 (3) | 0.059 (2) | 0.0049 (19) | −0.0029 (18) | −0.001 (2) |
| C7 | 0.050 (2) | 0.071 (3) | 0.045 (2) | −0.001 (2) | −0.0079 (18) | 0.004 (2) |
| C8 | 0.068 (3) | 0.058 (3) | 0.048 (2) | 0.000 (2) | −0.009 (2) | −0.006 (2) |
| C9 | 0.054 (2) | 0.046 (2) | 0.043 (2) | 0.0008 (18) | −0.0038 (18) | −0.0032 (17) |
| C10 | 0.051 (2) | 0.050 (2) | 0.042 (2) | −0.0013 (18) | 0.0088 (17) | 0.0000 (17) |
| C11 | 0.044 (2) | 0.044 (2) | 0.046 (2) | −0.0024 (17) | 0.0006 (16) | −0.0012 (17) |
| C12 | 0.051 (2) | 0.049 (2) | 0.045 (2) | −0.0043 (18) | 0.0032 (17) | −0.0042 (18) |
| C13 | 0.039 (2) | 0.0398 (19) | 0.049 (2) | 0.0019 (16) | 0.0013 (16) | −0.0016 (16) |
| C14 | 0.062 (3) | 0.063 (3) | 0.051 (2) | −0.013 (2) | 0.016 (2) | −0.008 (2) |
| C15 | 0.061 (3) | 0.059 (3) | 0.072 (3) | −0.022 (2) | 0.018 (2) | −0.006 (2) |
| C16 | 0.046 (2) | 0.043 (2) | 0.061 (2) | −0.0036 (18) | −0.0032 (18) | −0.0066 (19) |
| C17 | 0.057 (2) | 0.044 (2) | 0.049 (2) | −0.0011 (19) | 0.0013 (18) | −0.0017 (18) |
| C18 | 0.046 (2) | 0.045 (2) | 0.049 (2) | −0.0031 (17) | 0.0067 (17) | 0.0029 (17) |
| Br1—C10 | 1.854 (4) | C4—C5 | 1.383 (6) |
| Cl1—C4 | 1.722 (4) | C5—C6 | 1.392 (6) |
| Cl2—C6 | 1.717 (4) | C6—C7 | 1.377 (6) |
| Cl3—C16 | 1.735 (4) | C7—H7 | 0.9300 |
| F1—C1 | 1.305 (7) | C8—C9 | 1.431 (6) |
| F2—C1 | 1.283 (6) | C9—C10 | 1.398 (6) |
| F3—C1 | 1.273 (6) | C10—C11 | 1.373 (5) |
| N1—N2 | 1.343 (5) | C12—C13 | 1.459 (5) |
| N1—C11 | 1.376 (5) | C12—H12 | 0.9300 |
| N1—C5 | 1.427 (5) | C13—C18 | 1.383 (5) |
| N2—C9 | 1.335 (5) | C13—C14 | 1.390 (6) |
| N3—C8 | 1.138 (5) | C14—C15 | 1.384 (6) |
| N4—C12 | 1.276 (5) | C14—H14 | 0.9300 |
| N4—C11 | 1.380 (5) | C15—C16 | 1.357 (6) |
| C1—C2 | 1.498 (6) | C15—H15 | 0.9300 |
| C2—C7 | 1.365 (6) | C16—C17 | 1.376 (6) |
| C2—C3 | 1.380 (6) | C17—C18 | 1.372 (6) |
| C3—C4 | 1.388 (6) | C17—H17 | 0.9300 |
| C3—H3 | 0.9300 | C18—H18 | 0.9300 |
| N2—N1—C11 | 113.9 (3) | N2—C9—C10 | 112.4 (3) |
| N2—N1—C5 | 119.5 (3) | N2—C9—C8 | 120.0 (4) |
| C11—N1—C5 | 126.6 (3) | C10—C9—C8 | 127.6 (4) |
| C9—N2—N1 | 103.3 (3) | C11—C10—C9 | 105.7 (3) |
| C12—N4—C11 | 120.9 (3) | C11—C10—Br1 | 129.6 (3) |
| F3—C1—F2 | 109.1 (6) | C9—C10—Br1 | 124.6 (3) |
| F3—C1—F1 | 103.4 (6) | C10—C11—N1 | 104.7 (3) |
| F2—C1—F1 | 104.2 (5) | C10—C11—N4 | 138.1 (4) |
| F3—C1—C2 | 112.2 (4) | N1—C11—N4 | 116.9 (3) |
| F2—C1—C2 | 115.0 (4) | N4—C12—C13 | 121.2 (4) |
| F1—C1—C2 | 112.0 (5) | N4—C12—H12 | 119.4 |
| C7—C2—C3 | 121.9 (4) | C13—C12—H12 | 119.4 |
| C7—C2—C1 | 118.7 (4) | C18—C13—C14 | 118.6 (4) |
| C3—C2—C1 | 119.4 (4) | C18—C13—C12 | 121.8 (4) |
| C2—C3—C4 | 118.4 (4) | C14—C13—C12 | 119.6 (4) |
| C2—C3—H3 | 120.8 | C15—C14—C13 | 120.9 (4) |
| C4—C3—H3 | 120.8 | C15—C14—H14 | 119.5 |
| C5—C4—C3 | 120.8 (4) | C13—C14—H14 | 119.5 |
| C5—C4—Cl1 | 119.6 (3) | C16—C15—C14 | 118.6 (4) |
| C3—C4—Cl1 | 119.6 (3) | C16—C15—H15 | 120.7 |
| C4—C5—C6 | 119.0 (4) | C14—C15—H15 | 120.7 |
| C4—C5—N1 | 121.3 (4) | C15—C16—C17 | 122.0 (4) |
| C6—C5—N1 | 119.7 (4) | C15—C16—Cl3 | 119.1 (3) |
| C7—C6—C5 | 120.4 (4) | C17—C16—Cl3 | 118.9 (3) |
| C7—C6—Cl2 | 120.3 (3) | C18—C17—C16 | 119.1 (4) |
| C5—C6—Cl2 | 119.3 (3) | C18—C17—H17 | 120.5 |
| C2—C7—C6 | 119.5 (4) | C16—C17—H17 | 120.5 |
| C2—C7—H7 | 120.3 | C17—C18—C13 | 120.8 (4) |
| C6—C7—H7 | 120.3 | C17—C18—H18 | 119.6 |
| N3—C8—C9 | 178.4 (5) | C13—C18—H18 | 119.6 |
Experimental details
| Crystal data | |
| Chemical formula | C18H7BrCl3F3N4 |
| Mr | 522.54 |
| Crystal system, space group | Orthorhombic, Pbca |
| Temperature (K) | 298 |
| a, b, c (Å) | 10.0338 (7), 11.5819 (8), 34.499 (3) |
| V (Å3) | 4009.1 (5) |
| Z | 8 |
| Radiation type | Mo Kα |
| µ (mm−1) | 2.49 |
| Crystal size (mm) | 0.39 × 0.17 × 0.16 |
| Data collection | |
| Diffractometer | Bruker APEX area-detector |
| Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
| Tmin, Tmax | 0.444, 0.691 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 23679, 4736, 3014 |
| Rint | 0.036 |
| (sin θ/λ)max (Å−1) | 0.667 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.186, 1.04 |
| No. of reflections | 4736 |
| No. of parameters | 262 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 1.20, −0.84 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXL97.
| Br1—C10 | 1.854 (4) | N3—C8 | 1.138 (5) |
| F3—C1 | 1.273 (6) | N4—C12 | 1.276 (5) |
| N1—N2 | 1.343 (5) | N4—C11 | 1.380 (5) |
| N1—C11 | 1.376 (5) | C8—C9 | 1.431 (6) |
| N1—C5 | 1.427 (5) | C9—C10 | 1.398 (6) |
| N2—C9 | 1.335 (5) | C10—C11 | 1.373 (5) |
| N2—N1—C11 | 113.9 (3) | C10—C9—C8 | 127.6 (4) |
| N2—N1—C5 | 119.5 (3) | C11—C10—C9 | 105.7 (3) |
| C11—N1—C5 | 126.6 (3) | C11—C10—Br1 | 129.6 (3) |
| C9—N2—N1 | 103.3 (3) | C9—C10—Br1 | 124.6 (3) |
| C12—N4—C11 | 120.9 (3) | C10—C11—N1 | 104.7 (3) |
| F3—C1—F1 | 103.4 (6) | C10—C11—N4 | 138.1 (4) |
| N2—C9—C10 | 112.4 (3) | N1—C11—N4 | 116.9 (3) |
| N2—C9—C8 | 120.0 (4) |
The title compound, (I), (Fig. 1) is similar to the very effective insecticides used to treat animals such as cows and sheep (Philippe, 1997, 2000) and its structure is reported here. The molecule of (I) contains three essentially planar rings. The dihedral angles between the central pyrazole ring (C9—C11, N1, N2) and the benzene (C2—C7) and (C13—C16) ring planes are 84.3 (2)° and 68.5 (2)°, respectively.