Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028292/ci2393sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028292/ci2393Isup2.hkl |
CCDC reference: 654989
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.044
- wR factor = 0.131
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C21
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21' PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 71
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).
An anhydrous ethanol solution (50 ml) of 4,4,4-trifluoro-1-phenyl- butane-1,3-dione (2.16 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenyl-pyrazolidin-3-one (2.03 g, 10 mmol), and the mixture was stirred at 350 K for 6 h under N2, whereupon a yellow precipitate appeared. The product was isolated, recrystallized from anhydrous ethanol and then dried in vacuo to give pure compound (I) in 79% yield. Yellows single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol solution.
The trifluoromethyl group was treated as disordered over two orientations with refined occupancies of 0.802 (8) and 0.198 (8). All C—F bond lengths were restrained to 1.35 (1) Å, and the C20—C21 and C20—C21' distances were restrained to 1.52 (1) Å. The F···F distances were restrained to be equal, within a standard deviation of 0.01 Å. The displacement parameters of the disordered atoms were restrained to approximately isotropic behaviour. The N-bound H atom was located in a difference Fourier map and its positional parameters were refined, with Uiso(H) = 1.2Ueq(N). C-bound H atoms were included in calculated positions, with C—H = 0.93 (aromatic) or 0.96 Å (methyl), and refined using a riding model, with Uiso(H) = 1.2Ueq(C) for aromatic H or 1.5Ueq(C) for methyl H atoms.
In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).
In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. The pyrazole ring (C1—C3/N1/N2) is approximately planar, with a maximum deviation from the mean plane of 0.046 (1) Å for atom N1. The least-squares plane through the pyrazole ring forms dihedral angles of 47.61 (9) and 69.39 (8)°, respectively, with the C5—C10 and C13—C18 phenyl rings. The two phenyl rings are inclined at an angle of 80.70 (8)°.
An intramolecular N—H···O hydrogen bond stabilizes the molecular conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into centrosymmetric dimers as illustrated in Fig. 2.
For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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, 1997); software used to prepare material for publication: SHELXTL.
C21H18F3N3O2 | F(000) = 832 |
Mr = 401.38 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2616 reflections |
a = 13.452 (4) Å | θ = 2.3–23.6° |
b = 6.3930 (18) Å | µ = 0.11 mm−1 |
c = 23.466 (7) Å | T = 294 K |
β = 90.571 (5)° | Block, yellow |
V = 2017.9 (10) Å3 | 0.22 × 0.20 × 0.14 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3554 independent reflections |
Radiation source: fine-focus sealed tube | 2134 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→13 |
Tmin = 0.977, Tmax = 0.985 | k = −7→7 |
9666 measured reflections | l = −27→27 |
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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.059P)2 + 0.2821P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3554 reflections | Δρmax = 0.19 e Å−3 |
306 parameters | Δρmin = −0.16 e Å−3 |
71 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0114 (15) |
C21H18F3N3O2 | V = 2017.9 (10) Å3 |
Mr = 401.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.452 (4) Å | µ = 0.11 mm−1 |
b = 6.3930 (18) Å | T = 294 K |
c = 23.466 (7) Å | 0.22 × 0.20 × 0.14 mm |
β = 90.571 (5)° |
Bruker SMART CCD area-detector diffractometer | 3554 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2134 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.985 | Rint = 0.047 |
9666 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 71 restraints |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.19 e Å−3 |
3554 reflections | Δρmin = −0.16 e Å−3 |
306 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 | Occ. (<1) | |
C21 | 0.0597 (4) | −0.1194 (12) | 0.6599 (2) | 0.075 (3) | 0.802 (8) |
F1 | 0.0622 (5) | −0.3257 (6) | 0.65744 (17) | 0.1370 (19) | 0.802 (8) |
F2 | −0.0333 (2) | −0.0639 (9) | 0.67356 (15) | 0.1254 (19) | 0.802 (8) |
F3 | 0.1167 (3) | −0.0624 (9) | 0.70432 (16) | 0.113 (2) | 0.802 (8) |
C21' | 0.0663 (11) | −0.082 (2) | 0.6640 (4) | 0.077 (14) | 0.198 (8) |
F1' | 0.0020 (11) | −0.242 (3) | 0.6645 (5) | 0.086 (5) | 0.198 (8) |
F2' | 0.0267 (16) | 0.067 (2) | 0.6971 (6) | 0.132 (7) | 0.198 (8) |
F3' | 0.1472 (9) | −0.151 (3) | 0.6925 (8) | 0.104 (6) | 0.198 (8) |
N1 | 0.28293 (14) | 0.2485 (3) | 0.36876 (8) | 0.0415 (5) | |
N2 | 0.21147 (14) | 0.4106 (3) | 0.36303 (8) | 0.0430 (5) | |
N3 | 0.15442 (15) | 0.2092 (3) | 0.50379 (8) | 0.0426 (5) | |
O1 | 0.31148 (13) | −0.0196 (3) | 0.43548 (7) | 0.0588 (5) | |
O2 | 0.03316 (13) | −0.0629 (3) | 0.56238 (8) | 0.0630 (6) | |
C1 | 0.26854 (17) | 0.1439 (4) | 0.42103 (10) | 0.0397 (6) | |
C2 | 0.19382 (16) | 0.2675 (4) | 0.44969 (9) | 0.0376 (6) | |
C3 | 0.16334 (17) | 0.4250 (4) | 0.41474 (10) | 0.0422 (6) | |
C4 | 0.0920 (2) | 0.5991 (5) | 0.42645 (13) | 0.0660 (8) | |
H4A | 0.0563 | 0.5693 | 0.4607 | 0.099* | |
H4B | 0.0459 | 0.6119 | 0.3951 | 0.099* | |
H4C | 0.1281 | 0.7277 | 0.4310 | 0.099* | |
C5 | 0.31870 (18) | 0.1449 (4) | 0.31851 (10) | 0.0433 (6) | |
C6 | 0.2606 (2) | 0.1327 (4) | 0.26916 (11) | 0.0561 (7) | |
H6 | 0.1983 | 0.1958 | 0.2675 | 0.067* | |
C7 | 0.2972 (3) | 0.0248 (5) | 0.22233 (12) | 0.0746 (10) | |
H7 | 0.2594 | 0.0168 | 0.1890 | 0.090* | |
C8 | 0.3894 (3) | −0.0707 (5) | 0.22489 (14) | 0.0791 (10) | |
H8 | 0.4129 | −0.1435 | 0.1935 | 0.095* | |
C9 | 0.4465 (2) | −0.0581 (5) | 0.27394 (14) | 0.0691 (9) | |
H9 | 0.5084 | −0.1231 | 0.2756 | 0.083* | |
C10 | 0.41182 (19) | 0.0510 (4) | 0.32061 (11) | 0.0537 (7) | |
H10 | 0.4509 | 0.0616 | 0.3534 | 0.064* | |
C11 | 0.2445 (2) | 0.5981 (4) | 0.33217 (12) | 0.0613 (8) | |
H11A | 0.1883 | 0.6860 | 0.3240 | 0.092* | |
H11B | 0.2751 | 0.5571 | 0.2971 | 0.092* | |
H11C | 0.2917 | 0.6736 | 0.3552 | 0.092* | |
C12 | 0.20566 (17) | 0.2186 (4) | 0.55357 (10) | 0.0406 (6) | |
C13 | 0.29783 (17) | 0.3490 (4) | 0.55658 (9) | 0.0408 (6) | |
C14 | 0.2988 (2) | 0.5560 (4) | 0.53797 (11) | 0.0510 (7) | |
H14 | 0.2410 | 0.6150 | 0.5229 | 0.061* | |
C15 | 0.3848 (2) | 0.6748 (5) | 0.54162 (11) | 0.0585 (8) | |
H15 | 0.3846 | 0.8128 | 0.5291 | 0.070* | |
C16 | 0.4714 (2) | 0.5874 (5) | 0.56408 (11) | 0.0611 (8) | |
H16 | 0.5293 | 0.6665 | 0.5661 | 0.073* | |
C17 | 0.47138 (19) | 0.3839 (5) | 0.58334 (11) | 0.0583 (8) | |
H17 | 0.5293 | 0.3261 | 0.5985 | 0.070* | |
C18 | 0.38510 (18) | 0.2647 (4) | 0.58015 (10) | 0.0503 (7) | |
H18 | 0.3853 | 0.1280 | 0.5937 | 0.060* | |
C19 | 0.17242 (18) | 0.1156 (4) | 0.60245 (10) | 0.0483 (7) | |
H19 | 0.2078 | 0.1356 | 0.6363 | 0.058* | |
C20 | 0.08888 (19) | −0.0162 (4) | 0.60346 (10) | 0.0499 (7) | |
H3 | 0.0982 (19) | 0.129 (4) | 0.5052 (10) | 0.060 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C21 | 0.072 (4) | 0.092 (4) | 0.060 (4) | −0.039 (4) | −0.013 (3) | 0.020 (3) |
F1 | 0.187 (5) | 0.096 (3) | 0.127 (3) | −0.041 (3) | −0.034 (3) | 0.058 (2) |
F2 | 0.087 (2) | 0.198 (5) | 0.092 (2) | −0.018 (3) | 0.0368 (17) | 0.033 (3) |
F3 | 0.116 (3) | 0.171 (5) | 0.0502 (18) | −0.072 (3) | −0.021 (2) | 0.030 (2) |
C21' | 0.069 (16) | 0.084 (15) | 0.077 (17) | −0.017 (9) | −0.012 (10) | 0.005 (9) |
F1' | 0.095 (8) | 0.098 (9) | 0.065 (6) | −0.059 (7) | −0.018 (6) | 0.028 (6) |
F2' | 0.164 (11) | 0.133 (10) | 0.100 (8) | 0.007 (8) | 0.042 (8) | 0.004 (7) |
F3' | 0.113 (9) | 0.118 (9) | 0.080 (9) | 0.023 (7) | −0.015 (6) | 0.044 (7) |
N1 | 0.0451 (12) | 0.0405 (12) | 0.0390 (12) | 0.0028 (10) | 0.0033 (9) | 0.0038 (10) |
N2 | 0.0476 (12) | 0.0350 (12) | 0.0464 (12) | 0.0020 (10) | 0.0008 (9) | 0.0058 (10) |
N3 | 0.0363 (12) | 0.0532 (14) | 0.0381 (12) | −0.0100 (11) | 0.0011 (9) | −0.0004 (10) |
O1 | 0.0714 (13) | 0.0541 (12) | 0.0509 (11) | 0.0188 (10) | 0.0025 (9) | 0.0099 (9) |
O2 | 0.0535 (11) | 0.0818 (15) | 0.0536 (12) | −0.0217 (10) | −0.0111 (9) | 0.0076 (10) |
C1 | 0.0414 (14) | 0.0397 (15) | 0.0378 (14) | −0.0034 (12) | −0.0059 (11) | 0.0006 (12) |
C2 | 0.0350 (12) | 0.0428 (15) | 0.0350 (13) | −0.0037 (11) | −0.0008 (10) | −0.0007 (11) |
C3 | 0.0379 (13) | 0.0436 (15) | 0.0450 (14) | −0.0007 (12) | −0.0034 (11) | −0.0005 (12) |
C4 | 0.0650 (19) | 0.062 (2) | 0.071 (2) | 0.0186 (16) | 0.0049 (15) | 0.0022 (16) |
C5 | 0.0517 (15) | 0.0386 (14) | 0.0396 (14) | −0.0074 (12) | 0.0097 (12) | 0.0043 (11) |
C6 | 0.0706 (19) | 0.0545 (18) | 0.0431 (16) | −0.0030 (15) | 0.0014 (14) | 0.0057 (14) |
C7 | 0.118 (3) | 0.065 (2) | 0.0412 (17) | −0.003 (2) | 0.0051 (17) | 0.0016 (15) |
C8 | 0.123 (3) | 0.058 (2) | 0.057 (2) | 0.003 (2) | 0.036 (2) | −0.0019 (17) |
C9 | 0.076 (2) | 0.059 (2) | 0.072 (2) | 0.0045 (16) | 0.0301 (18) | −0.0011 (17) |
C10 | 0.0529 (17) | 0.0498 (17) | 0.0587 (17) | −0.0020 (14) | 0.0120 (13) | 0.0006 (14) |
C11 | 0.077 (2) | 0.0433 (17) | 0.0640 (19) | −0.0055 (15) | 0.0067 (15) | 0.0143 (14) |
C12 | 0.0384 (13) | 0.0426 (15) | 0.0407 (14) | 0.0008 (12) | −0.0010 (11) | −0.0055 (12) |
C13 | 0.0406 (14) | 0.0467 (16) | 0.0351 (13) | −0.0037 (12) | −0.0009 (10) | −0.0038 (11) |
C14 | 0.0545 (16) | 0.0457 (17) | 0.0527 (16) | −0.0052 (14) | −0.0097 (13) | −0.0047 (13) |
C15 | 0.073 (2) | 0.0495 (18) | 0.0526 (17) | −0.0183 (16) | −0.0052 (14) | −0.0031 (13) |
C16 | 0.0593 (19) | 0.077 (2) | 0.0473 (16) | −0.0283 (17) | 0.0007 (14) | −0.0087 (16) |
C17 | 0.0441 (16) | 0.079 (2) | 0.0516 (17) | −0.0075 (15) | −0.0051 (12) | 0.0012 (15) |
C18 | 0.0488 (15) | 0.0551 (17) | 0.0469 (15) | −0.0038 (14) | −0.0046 (12) | 0.0039 (13) |
C19 | 0.0469 (15) | 0.0584 (18) | 0.0395 (15) | −0.0097 (14) | −0.0056 (11) | 0.0008 (13) |
C20 | 0.0473 (15) | 0.0574 (18) | 0.0449 (15) | −0.0058 (14) | −0.0047 (12) | 0.0066 (13) |
C21—F1 | 1.320 (7) | C6—H6 | 0.93 |
C21—F3 | 1.338 (6) | C7—C8 | 1.382 (5) |
C21—F2 | 1.342 (5) | C7—H7 | 0.93 |
C21—C20 | 1.535 (5) | C8—C9 | 1.380 (4) |
C21'—F1' | 1.337 (10) | C8—H8 | 0.93 |
C21'—F2' | 1.342 (10) | C9—C10 | 1.384 (4) |
C21'—F3' | 1.345 (10) | C9—H9 | 0.93 |
C21'—C20 | 1.516 (10) | C10—H10 | 0.93 |
N1—C1 | 1.412 (3) | C11—H11A | 0.96 |
N1—N2 | 1.419 (3) | C11—H11B | 0.96 |
N1—C5 | 1.440 (3) | C11—H11C | 0.96 |
N2—C3 | 1.384 (3) | C12—C19 | 1.400 (3) |
N2—C11 | 1.472 (3) | C12—C13 | 1.495 (3) |
N3—C12 | 1.352 (3) | C13—C14 | 1.394 (4) |
N3—C2 | 1.430 (3) | C13—C18 | 1.401 (3) |
N3—H3 | 0.92 (3) | C14—C15 | 1.387 (3) |
O1—C1 | 1.240 (3) | C14—H14 | 0.93 |
O2—C20 | 1.251 (3) | C15—C16 | 1.390 (4) |
C1—C2 | 1.450 (3) | C15—H15 | 0.93 |
C2—C3 | 1.359 (3) | C16—C17 | 1.377 (4) |
C3—C4 | 1.497 (4) | C16—H16 | 0.93 |
C4—H4A | 0.96 | C17—C18 | 1.390 (4) |
C4—H4B | 0.96 | C17—H17 | 0.93 |
C4—H4C | 0.96 | C18—H18 | 0.93 |
C5—C10 | 1.389 (3) | C19—C20 | 1.405 (3) |
C5—C6 | 1.393 (3) | C19—H19 | 0.93 |
C6—C7 | 1.392 (4) | ||
F1—C21—F3 | 107.0 (4) | C9—C8—C7 | 120.1 (3) |
F1—C21—F2 | 107.4 (6) | C9—C8—H8 | 119.9 |
F3—C21—F2 | 105.7 (5) | C7—C8—H8 | 119.9 |
F1—C21—C20 | 112.6 (5) | C8—C9—C10 | 120.0 (3) |
F3—C21—C20 | 113.9 (5) | C8—C9—H9 | 120.0 |
F2—C21—C20 | 109.8 (4) | C10—C9—H9 | 120.0 |
F1'—C21'—F2' | 106.0 (8) | C9—C10—C5 | 120.0 (3) |
F1'—C21'—F3' | 105.5 (8) | C9—C10—H10 | 120.0 |
F2'—C21'—F3' | 105.5 (8) | C5—C10—H10 | 120.0 |
F1'—C21'—C20 | 110.8 (10) | N2—C11—H11A | 109.5 |
F2'—C21'—C20 | 115.5 (11) | N2—C11—H11B | 109.5 |
F3'—C21'—C20 | 112.8 (13) | H11A—C11—H11B | 109.5 |
C1—N1—N2 | 109.25 (17) | N2—C11—H11C | 109.5 |
C1—N1—C5 | 122.9 (2) | H11A—C11—H11C | 109.5 |
N2—N1—C5 | 119.35 (18) | H11B—C11—H11C | 109.5 |
C3—N2—N1 | 106.72 (17) | N3—C12—C19 | 121.5 (2) |
C3—N2—C11 | 121.6 (2) | N3—C12—C13 | 118.8 (2) |
N1—N2—C11 | 115.72 (19) | C19—C12—C13 | 119.7 (2) |
C12—N3—C2 | 124.4 (2) | C14—C13—C18 | 118.6 (2) |
C12—N3—H3 | 114.0 (16) | C14—C13—C12 | 121.6 (2) |
C2—N3—H3 | 119.6 (16) | C18—C13—C12 | 119.7 (2) |
O1—C1—N1 | 124.7 (2) | C15—C14—C13 | 120.7 (3) |
O1—C1—C2 | 131.0 (2) | C15—C14—H14 | 119.6 |
N1—C1—C2 | 104.3 (2) | C13—C14—H14 | 119.6 |
C3—C2—N3 | 128.1 (2) | C14—C15—C16 | 119.9 (3) |
C3—C2—C1 | 109.3 (2) | C14—C15—H15 | 120.1 |
N3—C2—C1 | 122.3 (2) | C16—C15—H15 | 120.1 |
C2—C3—N2 | 109.8 (2) | C17—C16—C15 | 120.1 (3) |
C2—C3—C4 | 129.0 (2) | C17—C16—H16 | 119.9 |
N2—C3—C4 | 121.1 (2) | C15—C16—H16 | 119.9 |
C3—C4—H4A | 109.5 | C16—C17—C18 | 120.2 (3) |
C3—C4—H4B | 109.5 | C16—C17—H17 | 119.9 |
H4A—C4—H4B | 109.5 | C18—C17—H17 | 119.9 |
C3—C4—H4C | 109.5 | C17—C18—C13 | 120.4 (3) |
H4A—C4—H4C | 109.5 | C17—C18—H18 | 119.8 |
H4B—C4—H4C | 109.5 | C13—C18—H18 | 119.8 |
C10—C5—C6 | 120.3 (2) | C12—C19—C20 | 123.9 (2) |
C10—C5—N1 | 118.6 (2) | C12—C19—H19 | 118.0 |
C6—C5—N1 | 121.2 (2) | C20—C19—H19 | 118.0 |
C7—C6—C5 | 118.9 (3) | O2—C20—C19 | 127.1 (2) |
C7—C6—H6 | 120.5 | O2—C20—C21' | 122.1 (6) |
C5—C6—H6 | 120.5 | C19—C20—C21' | 110.5 (6) |
C8—C7—C6 | 120.6 (3) | O2—C20—C21 | 113.9 (3) |
C8—C7—H7 | 119.7 | C19—C20—C21 | 118.9 (3) |
C6—C7—H7 | 119.7 | ||
C1—N1—N2—C3 | 8.5 (2) | N3—C12—C13—C14 | 50.5 (3) |
C5—N1—N2—C3 | 157.42 (19) | C19—C12—C13—C14 | −127.2 (3) |
C1—N1—N2—C11 | 147.2 (2) | N3—C12—C13—C18 | −131.4 (2) |
C5—N1—N2—C11 | −63.9 (3) | C19—C12—C13—C18 | 50.9 (3) |
N2—N1—C1—O1 | 171.3 (2) | C18—C13—C14—C15 | 1.3 (4) |
C5—N1—C1—O1 | 23.7 (3) | C12—C13—C14—C15 | 179.4 (2) |
N2—N1—C1—C2 | −7.2 (2) | C13—C14—C15—C16 | 0.0 (4) |
C5—N1—C1—C2 | −154.8 (2) | C14—C15—C16—C17 | −0.8 (4) |
C12—N3—C2—C3 | −116.3 (3) | C15—C16—C17—C18 | 0.3 (4) |
C12—N3—C2—C1 | 71.0 (3) | C16—C17—C18—C13 | 1.0 (4) |
O1—C1—C2—C3 | −175.0 (2) | C14—C13—C18—C17 | −1.8 (4) |
N1—C1—C2—C3 | 3.4 (2) | C12—C13—C18—C17 | −179.9 (2) |
O1—C1—C2—N3 | −1.1 (4) | N3—C12—C19—C20 | 4.7 (4) |
N1—C1—C2—N3 | 177.23 (19) | C13—C12—C19—C20 | −177.6 (2) |
N3—C2—C3—N2 | −171.6 (2) | C12—C19—C20—O2 | 0.7 (5) |
C1—C2—C3—N2 | 1.8 (3) | C12—C19—C20—C21' | −173.4 (6) |
N3—C2—C3—C4 | 10.3 (4) | C12—C19—C20—C21 | −179.7 (3) |
C1—C2—C3—C4 | −176.2 (2) | F1'—C21'—C20—O2 | 19.4 (13) |
N1—N2—C3—C2 | −6.3 (2) | F2'—C21'—C20—O2 | −101.2 (12) |
C11—N2—C3—C2 | −142.0 (2) | F3'—C21'—C20—O2 | 137.3 (11) |
N1—N2—C3—C4 | 172.0 (2) | F1'—C21'—C20—C19 | −166.2 (10) |
C11—N2—C3—C4 | 36.2 (3) | F2'—C21'—C20—C19 | 73.2 (13) |
C1—N1—C5—C10 | −60.4 (3) | F3'—C21'—C20—C19 | −48.2 (13) |
N2—N1—C5—C10 | 155.0 (2) | F1'—C21'—C20—C21 | −19 (3) |
C1—N1—C5—C6 | 117.7 (3) | F2'—C21'—C20—C21 | −140 (5) |
N2—N1—C5—C6 | −26.8 (3) | F3'—C21'—C20—C21 | 99 (4) |
C10—C5—C6—C7 | 0.2 (4) | F1—C21—C20—O2 | 60.7 (6) |
N1—C5—C6—C7 | −177.9 (2) | F3—C21—C20—O2 | −177.3 (5) |
C5—C6—C7—C8 | 0.6 (4) | F2—C21—C20—O2 | −58.9 (6) |
C6—C7—C8—C9 | −0.6 (5) | F1—C21—C20—C19 | −119.0 (5) |
C7—C8—C9—C10 | −0.3 (5) | F3—C21—C20—C19 | 3.1 (7) |
C8—C9—C10—C5 | 1.2 (4) | F2—C21—C20—C19 | 121.4 (5) |
C6—C5—C10—C9 | −1.1 (4) | F1—C21—C20—C21' | −155 (4) |
N1—C5—C10—C9 | 177.0 (2) | F3—C21—C20—C21' | −33 (4) |
C2—N3—C12—C19 | −164.9 (2) | F2—C21—C20—C21' | 86 (4) |
C2—N3—C12—C13 | 17.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.92 (3) | 2.02 (3) | 2.761 (3) | 137 (2) |
N3—H3···O2i | 0.92 (3) | 2.40 (3) | 3.094 (3) | 133 (2) |
Symmetry code: (i) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H18F3N3O2 |
Mr | 401.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 13.452 (4), 6.3930 (18), 23.466 (7) |
β (°) | 90.571 (5) |
V (Å3) | 2017.9 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.22 × 0.20 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.977, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9666, 3554, 2134 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.131, 1.02 |
No. of reflections | 3554 |
No. of parameters | 306 |
No. of restraints | 71 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.16 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.92 (3) | 2.02 (3) | 2.761 (3) | 137 (2) |
N3—H3···O2i | 0.92 (3) | 2.40 (3) | 3.094 (3) | 133 (2) |
Symmetry code: (i) −x, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).
In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. The pyrazole ring (C1—C3/N1/N2) is approximately planar, with a maximum deviation from the mean plane of 0.046 (1) Å for atom N1. The least-squares plane through the pyrazole ring forms dihedral angles of 47.61 (9) and 69.39 (8)°, respectively, with the C5—C10 and C13—C18 phenyl rings. The two phenyl rings are inclined at an angle of 80.70 (8)°.
An intramolecular N—H···O hydrogen bond stabilizes the molecular conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into centrosymmetric dimers as illustrated in Fig. 2.