Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031686/hk2281sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031686/hk2281Isup2.hkl |
CCDC reference: 657681
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.077
- wR factor = 0.225
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 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
For bond-length data, see: Allen et al. (1987). For related literature, see: Masahiko & Kazuyoshi (1999); Zhu et al. (2004).
For the preparation of the title compound, (I), 5-(4-Methoxyphenyl)-1-p -tolylpyrazolidin-3-one, (II), was firstly prepared and recrystallized from ethanol, according to the literature method (Masahiko & Kazuyoshi, 1999). Then, compound (II) (4.2 g, 15 mmol) was dissolved in dimethyl- formamide (100 ml) and mixed with FeCl3 (0.3 g, 1.5 mmol) (Zhu et al., 2004). The mixture was heated to 353 K and maintained at that temperature for 1 h, and then stirred for 12 h without heating. The reaction mixture was then poured into water (500 ml). The precipitate which formed was filtered off, washed with water and dried under reduced pressure. The crude product was then crystallized from ethanol to give (I) (yield; 2.8 g, 10 mmol). Crystals of (I) suitable for X-ray analysis were grown by slow evaporation of a solution in acetic ether at room temperature about 7 d.
H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.2 for aromatic H, and x = 1.5 for all other H atoms.
In the process of synthesis, we obtained the title compound, (I), and we herein report its crystal structure.
The asymmetric unit of the title compound, (I), contains two crystallographically independent molecules, with methylphenyl and methoxyphenyl substituents in different orientations with respect to the pyrazole ring (Fig. 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987).
The rings A (N1/N2/C8—C10), B (C2—C7), C (C11—C16) and A' (N3/N4/C25—C27), B' (C19—C24), C' (C28—C33) are, of course, planar and they are oriented at diheral angles of A/B = 53.93 (2)°, A/C = 39.63 (3)°, B/C = 64.37 (2)° and A'/B' = 45.45 (2)°, A'/C' = 48.66 (3)°, B'/C' = 51.98 (3)°.
In the crystal structure, intermolecular O—H···N and C—H···O hydrogen bonds (Table 1) link the molecules, in which O—H···N bonds generate the centrosymmetric dimers, and they are connected by C—H···O bonds to generate one-dimensional double-stranded chains (Fig. 2).
For bond-length data, see: Allen et al. (1987). For related literature, see: Masahiko & Kazuyoshi (1999); Zhu et al. (2004).
Data collection: CAD-4 Software (Enraf-Nonius, 1985); 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 (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C17H16N2O2 | Z = 4 |
Mr = 280.32 | F(000) = 592 |
Triclinic, P1 | Dx = 1.271 Mg m−3 |
Hall symbol: -P 1 | Melting point: 515 K |
a = 9.2520 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.160 (2) Å | Cell parameters from 25 reflections |
c = 16.338 (3) Å | θ = 9–12° |
α = 90.72 (3)° | µ = 0.09 mm−1 |
β = 91.97 (3)° | T = 298 K |
γ = 107.34 (3)° | Needle, colorless |
V = 1464.7 (6) Å3 | 0.40 × 0.10 × 0.10 mm |
Enraf-Nonius CAD-4 diffractometer | 2899 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 26.0°, θmin = 1.3° |
ω/2θ scans | h = −11→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.975, Tmax = 0.990 | l = 0→20 |
6130 measured reflections | 3 standard reflections every 120 min |
5754 independent reflections | intensity decay: none |
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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.225 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.05P)2 + 2.P] where P = (Fo2 + 2Fc2)/3 |
5754 reflections | (Δ/σ)max = 0.002 |
379 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C17H16N2O2 | γ = 107.34 (3)° |
Mr = 280.32 | V = 1464.7 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.2520 (19) Å | Mo Kα radiation |
b = 10.160 (2) Å | µ = 0.09 mm−1 |
c = 16.338 (3) Å | T = 298 K |
α = 90.72 (3)° | 0.40 × 0.10 × 0.10 mm |
β = 91.97 (3)° |
Enraf-Nonius CAD-4 diffractometer | 2899 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.056 |
Tmin = 0.975, Tmax = 0.990 | 3 standard reflections every 120 min |
6130 measured reflections | intensity decay: none |
5754 independent reflections |
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.225 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.32 e Å−3 |
5754 reflections | Δρmin = −0.28 e Å−3 |
379 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 | ||
O1 | 0.3812 (4) | 0.3092 (3) | 0.4980 (3) | 0.0922 (13) | |
H1E | 0.4660 | 0.3544 | 0.5206 | 0.111* | |
O2 | −0.4318 (4) | 0.4092 (4) | 0.2242 (2) | 0.0857 (11) | |
N1 | 0.3451 (4) | 0.5152 (4) | 0.4561 (3) | 0.0688 (11) | |
N2 | 0.2291 (4) | 0.5472 (4) | 0.4138 (2) | 0.0651 (11) | |
C1 | 0.3833 (6) | 1.1069 (5) | 0.3103 (4) | 0.0936 (18) | |
H1B | 0.4116 | 1.1693 | 0.3568 | 0.140* | |
H1C | 0.3011 | 1.1249 | 0.2797 | 0.140* | |
H1D | 0.4684 | 1.1197 | 0.2760 | 0.140* | |
C2 | 0.3336 (5) | 0.9587 (5) | 0.3397 (3) | 0.0626 (12) | |
C3 | 0.2867 (5) | 0.8513 (5) | 0.2808 (3) | 0.0646 (13) | |
H3A | 0.2808 | 0.8708 | 0.2255 | 0.078* | |
C4 | 0.2493 (5) | 0.7155 (5) | 0.3057 (3) | 0.0639 (13) | |
H4A | 0.2175 | 0.6435 | 0.2673 | 0.077* | |
C5 | 0.2593 (5) | 0.6883 (5) | 0.3867 (3) | 0.0611 (12) | |
C6 | 0.3034 (5) | 0.7945 (5) | 0.4455 (3) | 0.0662 (13) | |
H6A | 0.3060 | 0.7753 | 0.5010 | 0.079* | |
C7 | 0.3429 (5) | 0.9281 (5) | 0.4198 (4) | 0.0709 (14) | |
H7A | 0.3770 | 0.9997 | 0.4585 | 0.085* | |
C8 | 0.2978 (6) | 0.3788 (5) | 0.4612 (3) | 0.0725 (14) | |
C9 | 0.1579 (5) | 0.3230 (5) | 0.4217 (3) | 0.0740 (14) | |
H9A | 0.1031 | 0.2301 | 0.4164 | 0.089* | |
C10 | 0.1164 (5) | 0.4329 (5) | 0.3919 (3) | 0.0663 (13) | |
C11 | −0.0252 (5) | 0.4331 (5) | 0.3476 (3) | 0.0617 (12) | |
C12 | −0.0911 (5) | 0.3309 (5) | 0.2886 (3) | 0.0726 (14) | |
H12A | −0.0419 | 0.2663 | 0.2754 | 0.087* | |
C13 | −0.2264 (5) | 0.3234 (5) | 0.2498 (3) | 0.0763 (15) | |
H13A | −0.2710 | 0.2515 | 0.2126 | 0.092* | |
C14 | −0.2975 (5) | 0.4228 (5) | 0.2658 (3) | 0.0670 (13) | |
C15 | −0.2348 (6) | 0.5255 (6) | 0.3244 (4) | 0.0844 (17) | |
H15A | −0.2834 | 0.5907 | 0.3373 | 0.101* | |
C16 | −0.0983 (5) | 0.5290 (5) | 0.3634 (3) | 0.0760 (15) | |
H16A | −0.0547 | 0.5993 | 0.4017 | 0.091* | |
C17 | −0.5285 (6) | 0.4835 (7) | 0.2533 (4) | 0.101 (2) | |
H17A | −0.6190 | 0.4625 | 0.2188 | 0.151* | |
H17B | −0.4771 | 0.5806 | 0.2523 | 0.151* | |
H17C | −0.5547 | 0.4576 | 0.3084 | 0.151* | |
O3 | 0.5366 (4) | 0.9271 (4) | −0.1042 (2) | 0.0901 (12) | |
H3C | 0.4917 | 0.9760 | −0.0826 | 0.135* | |
O4 | 1.2470 (4) | 0.5589 (4) | 0.0961 (2) | 0.0795 (10) | |
N3 | 0.6276 (4) | 0.9259 (4) | 0.0300 (2) | 0.0618 (10) | |
N4 | 0.7377 (4) | 0.8768 (4) | 0.0654 (2) | 0.0609 (10) | |
C18 | 0.8710 (7) | 0.9521 (6) | 0.4095 (3) | 0.0938 (18) | |
H18A | 0.9787 | 0.9828 | 0.4203 | 0.141* | |
H18B | 0.8286 | 0.8649 | 0.4348 | 0.141* | |
H18C | 0.8269 | 1.0186 | 0.4315 | 0.141* | |
C19 | 0.8381 (5) | 0.9361 (5) | 0.3186 (3) | 0.0607 (12) | |
C20 | 0.9493 (5) | 0.9620 (5) | 0.2624 (3) | 0.0629 (12) | |
H20A | 1.0497 | 0.9923 | 0.2817 | 0.076* | |
C21 | 0.9209 (5) | 0.9459 (5) | 0.1793 (3) | 0.0586 (12) | |
H21A | 1.0001 | 0.9647 | 0.1435 | 0.070* | |
C22 | 0.7713 (5) | 0.9008 (4) | 0.1499 (3) | 0.0532 (11) | |
C23 | 0.6570 (5) | 0.8759 (5) | 0.2060 (3) | 0.0597 (12) | |
H23A | 0.5563 | 0.8462 | 0.1870 | 0.072* | |
C24 | 0.6890 (5) | 0.8938 (5) | 0.2871 (3) | 0.0687 (13) | |
H24A | 0.6099 | 0.8775 | 0.3229 | 0.082* | |
C25 | 0.6305 (6) | 0.8974 (5) | −0.0495 (3) | 0.0649 (13) | |
C26 | 0.7356 (6) | 0.8242 (5) | −0.0640 (3) | 0.0691 (13) | |
H26A | 0.7548 | 0.7895 | −0.1141 | 0.083* | |
C27 | 0.8022 (5) | 0.8151 (5) | 0.0092 (3) | 0.0593 (12) | |
C28 | 0.9197 (5) | 0.7482 (5) | 0.0309 (3) | 0.0578 (11) | |
C29 | 1.0511 (5) | 0.7743 (5) | −0.0123 (3) | 0.0696 (13) | |
H29A | 1.0642 | 0.8343 | −0.0559 | 0.083* | |
C30 | 1.1634 (5) | 0.7144 (5) | 0.0070 (3) | 0.0706 (14) | |
H30A | 1.2509 | 0.7346 | −0.0227 | 0.085* | |
C31 | 1.1442 (5) | 0.6256 (5) | 0.0699 (3) | 0.0602 (12) | |
C32 | 1.0140 (5) | 0.5950 (5) | 0.1143 (3) | 0.0623 (12) | |
H32A | 1.0013 | 0.5335 | 0.1570 | 0.075* | |
C33 | 0.9034 (5) | 0.6563 (5) | 0.0946 (3) | 0.0574 (11) | |
H33A | 0.8161 | 0.6357 | 0.1246 | 0.069* | |
C34 | 1.3763 (5) | 0.5759 (6) | 0.0480 (4) | 0.0854 (17) | |
H34A | 1.4398 | 0.5259 | 0.0718 | 0.128* | |
H34B | 1.4321 | 0.6721 | 0.0465 | 0.128* | |
H34C | 1.3443 | 0.5413 | −0.0067 | 0.128* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.060 (2) | 0.061 (2) | 0.148 (4) | 0.0090 (18) | −0.023 (2) | 0.020 (2) |
O2 | 0.057 (2) | 0.087 (3) | 0.109 (3) | 0.018 (2) | −0.025 (2) | −0.006 (2) |
N1 | 0.053 (2) | 0.059 (3) | 0.091 (3) | 0.012 (2) | −0.013 (2) | 0.006 (2) |
N2 | 0.052 (2) | 0.052 (2) | 0.087 (3) | 0.0116 (19) | −0.018 (2) | 0.003 (2) |
C1 | 0.078 (4) | 0.059 (3) | 0.135 (5) | 0.007 (3) | 0.003 (4) | 0.000 (3) |
C2 | 0.039 (2) | 0.054 (3) | 0.094 (4) | 0.013 (2) | −0.002 (2) | −0.002 (3) |
C3 | 0.047 (3) | 0.072 (3) | 0.076 (3) | 0.021 (2) | 0.000 (2) | −0.004 (3) |
C4 | 0.050 (3) | 0.062 (3) | 0.079 (3) | 0.019 (2) | −0.011 (2) | −0.018 (3) |
C5 | 0.047 (3) | 0.060 (3) | 0.075 (3) | 0.015 (2) | −0.008 (2) | −0.002 (3) |
C6 | 0.068 (3) | 0.064 (3) | 0.066 (3) | 0.019 (3) | −0.006 (2) | −0.008 (3) |
C7 | 0.057 (3) | 0.053 (3) | 0.100 (4) | 0.015 (2) | −0.010 (3) | −0.017 (3) |
C8 | 0.058 (3) | 0.067 (3) | 0.093 (4) | 0.021 (3) | −0.016 (3) | 0.004 (3) |
C9 | 0.053 (3) | 0.061 (3) | 0.099 (4) | 0.003 (2) | −0.003 (3) | 0.004 (3) |
C10 | 0.051 (3) | 0.062 (3) | 0.083 (3) | 0.014 (2) | −0.005 (2) | −0.005 (3) |
C11 | 0.046 (2) | 0.065 (3) | 0.070 (3) | 0.012 (2) | −0.009 (2) | −0.006 (2) |
C12 | 0.057 (3) | 0.065 (3) | 0.095 (4) | 0.020 (3) | −0.010 (3) | −0.008 (3) |
C13 | 0.057 (3) | 0.065 (3) | 0.102 (4) | 0.014 (3) | −0.019 (3) | −0.015 (3) |
C14 | 0.048 (3) | 0.068 (3) | 0.083 (3) | 0.017 (2) | −0.011 (2) | 0.000 (3) |
C15 | 0.062 (3) | 0.081 (4) | 0.112 (5) | 0.026 (3) | −0.014 (3) | −0.023 (3) |
C16 | 0.053 (3) | 0.075 (4) | 0.096 (4) | 0.016 (3) | −0.017 (3) | −0.022 (3) |
C17 | 0.063 (4) | 0.110 (5) | 0.136 (6) | 0.039 (4) | −0.018 (4) | −0.006 (4) |
O3 | 0.100 (3) | 0.116 (3) | 0.072 (2) | 0.064 (3) | −0.023 (2) | −0.017 (2) |
O4 | 0.057 (2) | 0.088 (3) | 0.102 (3) | 0.0357 (19) | 0.0013 (19) | 0.014 (2) |
N3 | 0.043 (2) | 0.072 (3) | 0.075 (3) | 0.0259 (19) | −0.0095 (18) | −0.007 (2) |
N4 | 0.050 (2) | 0.065 (3) | 0.068 (3) | 0.0202 (19) | −0.0099 (19) | −0.002 (2) |
C18 | 0.092 (4) | 0.085 (4) | 0.088 (4) | 0.005 (3) | −0.019 (3) | −0.004 (3) |
C19 | 0.056 (3) | 0.058 (3) | 0.068 (3) | 0.019 (2) | −0.009 (2) | −0.006 (2) |
C20 | 0.040 (2) | 0.071 (3) | 0.073 (3) | 0.012 (2) | −0.009 (2) | −0.007 (3) |
C21 | 0.044 (2) | 0.070 (3) | 0.060 (3) | 0.015 (2) | −0.005 (2) | −0.002 (2) |
C22 | 0.046 (2) | 0.048 (3) | 0.064 (3) | 0.013 (2) | 0.000 (2) | −0.003 (2) |
C23 | 0.039 (2) | 0.071 (3) | 0.070 (3) | 0.018 (2) | −0.003 (2) | −0.001 (2) |
C24 | 0.051 (3) | 0.087 (4) | 0.066 (3) | 0.017 (3) | 0.006 (2) | 0.002 (3) |
C25 | 0.067 (3) | 0.073 (3) | 0.058 (3) | 0.028 (3) | −0.011 (2) | −0.006 (2) |
C26 | 0.070 (3) | 0.085 (4) | 0.054 (3) | 0.026 (3) | 0.000 (2) | −0.010 (3) |
C27 | 0.048 (3) | 0.059 (3) | 0.071 (3) | 0.015 (2) | 0.003 (2) | −0.010 (2) |
C28 | 0.048 (3) | 0.054 (3) | 0.071 (3) | 0.015 (2) | 0.004 (2) | 0.001 (2) |
C29 | 0.064 (3) | 0.071 (3) | 0.079 (3) | 0.027 (3) | 0.013 (3) | 0.013 (3) |
C30 | 0.048 (3) | 0.065 (3) | 0.102 (4) | 0.022 (2) | 0.012 (3) | 0.007 (3) |
C31 | 0.050 (3) | 0.054 (3) | 0.076 (3) | 0.017 (2) | −0.007 (2) | −0.006 (2) |
C32 | 0.050 (3) | 0.064 (3) | 0.073 (3) | 0.018 (2) | 0.002 (2) | 0.001 (2) |
C33 | 0.046 (2) | 0.059 (3) | 0.067 (3) | 0.014 (2) | 0.000 (2) | 0.000 (2) |
C34 | 0.051 (3) | 0.089 (4) | 0.117 (5) | 0.025 (3) | −0.005 (3) | −0.007 (3) |
O1—C8 | 1.327 (5) | O3—C25 | 1.325 (5) |
O1—H1E | 0.8500 | O3—H3C | 0.8200 |
O2—C14 | 1.365 (5) | O4—C31 | 1.382 (5) |
O2—C17 | 1.420 (6) | O4—C34 | 1.423 (6) |
N1—C8 | 1.328 (6) | N3—C25 | 1.329 (6) |
N1—N2 | 1.378 (5) | N3—N4 | 1.374 (5) |
N2—C10 | 1.344 (6) | N4—C27 | 1.355 (5) |
N2—C5 | 1.454 (6) | N4—C22 | 1.407 (5) |
C1—C2 | 1.526 (7) | C18—C19 | 1.502 (7) |
C1—H1B | 0.9600 | C18—H18A | 0.9600 |
C1—H1C | 0.9600 | C18—H18B | 0.9600 |
C1—H1D | 0.9600 | C18—H18C | 0.9600 |
C2—C7 | 1.356 (7) | C19—C20 | 1.372 (6) |
C2—C3 | 1.403 (6) | C19—C24 | 1.395 (6) |
C3—C4 | 1.388 (6) | C20—C21 | 1.372 (6) |
C3—H3A | 0.9300 | C20—H20A | 0.9300 |
C4—C5 | 1.360 (6) | C21—C22 | 1.388 (6) |
C4—H4A | 0.9300 | C21—H21A | 0.9300 |
C5—C6 | 1.392 (6) | C22—C23 | 1.391 (6) |
C6—C7 | 1.372 (7) | C23—C24 | 1.346 (6) |
C6—H6A | 0.9300 | C23—H23A | 0.9300 |
C7—H7A | 0.9300 | C24—H24A | 0.9300 |
C8—C9 | 1.382 (6) | C25—C26 | 1.413 (6) |
C9—C10 | 1.374 (6) | C26—C27 | 1.344 (6) |
C9—H9A | 0.9300 | C26—H26A | 0.9300 |
C10—C11 | 1.475 (6) | C27—C28 | 1.480 (6) |
C11—C16 | 1.368 (6) | C28—C29 | 1.386 (6) |
C11—C12 | 1.392 (6) | C28—C33 | 1.389 (6) |
C12—C13 | 1.365 (6) | C29—C30 | 1.382 (6) |
C12—H12A | 0.9300 | C29—H29A | 0.9300 |
C13—C14 | 1.387 (6) | C30—C31 | 1.356 (6) |
C13—H13A | 0.9300 | C30—H30A | 0.9300 |
C14—C15 | 1.385 (7) | C31—C32 | 1.384 (6) |
C15—C16 | 1.385 (6) | C32—C33 | 1.379 (6) |
C15—H15A | 0.9300 | C32—H32A | 0.9300 |
C16—H16A | 0.9300 | C33—H33A | 0.9300 |
C17—H17A | 0.9600 | C34—H34A | 0.9600 |
C17—H17B | 0.9600 | C34—H34B | 0.9600 |
C17—H17C | 0.9600 | C34—H34C | 0.9600 |
C8—O1—H1E | 118.4 | C25—O3—H3C | 109.5 |
C14—O2—C17 | 118.8 (4) | C31—O4—C34 | 116.5 (4) |
C8—N1—N2 | 104.5 (4) | C25—N3—N4 | 104.2 (4) |
C10—N2—N1 | 111.3 (4) | C27—N4—N3 | 111.7 (4) |
C10—N2—C5 | 130.5 (4) | C27—N4—C22 | 129.9 (4) |
N1—N2—C5 | 116.9 (4) | N3—N4—C22 | 118.4 (4) |
C2—C1—H1B | 109.5 | C19—C18—H18A | 109.5 |
C2—C1—H1C | 109.5 | C19—C18—H18B | 109.5 |
H1B—C1—H1C | 109.5 | H18A—C18—H18B | 109.5 |
C2—C1—H1D | 109.5 | C19—C18—H18C | 109.5 |
H1B—C1—H1D | 109.5 | H18A—C18—H18C | 109.5 |
H1C—C1—H1D | 109.5 | H18B—C18—H18C | 109.5 |
C7—C2—C3 | 119.4 (5) | C20—C19—C24 | 116.3 (4) |
C7—C2—C1 | 122.0 (5) | C20—C19—C18 | 123.2 (4) |
C3—C2—C1 | 118.4 (5) | C24—C19—C18 | 120.6 (5) |
C4—C3—C2 | 119.4 (5) | C21—C20—C19 | 123.8 (4) |
C4—C3—H3A | 120.3 | C21—C20—H20A | 118.1 |
C2—C3—H3A | 120.3 | C19—C20—H20A | 118.1 |
C5—C4—C3 | 119.7 (5) | C20—C21—C22 | 118.5 (4) |
C5—C4—H4A | 120.1 | C20—C21—H21A | 120.8 |
C3—C4—H4A | 120.1 | C22—C21—H21A | 120.8 |
C4—C5—C6 | 121.1 (5) | C21—C22—C23 | 118.5 (4) |
C4—C5—N2 | 120.7 (4) | C21—C22—N4 | 120.2 (4) |
C6—C5—N2 | 118.2 (4) | C23—C22—N4 | 121.3 (4) |
C7—C6—C5 | 118.5 (5) | C24—C23—C22 | 121.4 (4) |
C7—C6—H6A | 120.8 | C24—C23—H23A | 119.3 |
C5—C6—H6A | 120.8 | C22—C23—H23A | 119.3 |
C2—C7—C6 | 121.8 (5) | C23—C24—C19 | 121.5 (5) |
C2—C7—H7A | 119.1 | C23—C24—H24A | 119.2 |
C6—C7—H7A | 119.1 | C19—C24—H24A | 119.2 |
N1—C8—O1 | 122.1 (4) | O3—C25—N3 | 122.1 (4) |
N1—C8—C9 | 111.5 (4) | O3—C25—C26 | 126.8 (4) |
O1—C8—C9 | 126.3 (5) | N3—C25—C26 | 110.9 (4) |
C10—C9—C8 | 105.9 (5) | C27—C26—C25 | 105.9 (4) |
C10—C9—H9A | 127.1 | C27—C26—H26A | 127.0 |
C8—C9—H9A | 127.1 | C25—C26—H26A | 127.0 |
N2—C10—C9 | 106.8 (4) | C26—C27—N4 | 107.2 (4) |
N2—C10—C11 | 124.3 (4) | C26—C27—C28 | 129.7 (4) |
C9—C10—C11 | 128.9 (5) | N4—C27—C28 | 123.1 (4) |
C16—C11—C12 | 117.6 (4) | C29—C28—C33 | 117.1 (4) |
C16—C11—C10 | 122.6 (4) | C29—C28—C27 | 121.0 (4) |
C12—C11—C10 | 119.8 (4) | C33—C28—C27 | 121.9 (4) |
C13—C12—C11 | 121.3 (5) | C30—C29—C28 | 122.2 (5) |
C13—C12—H12A | 119.3 | C30—C29—H29A | 118.9 |
C11—C12—H12A | 119.3 | C28—C29—H29A | 118.9 |
C12—C13—C14 | 120.0 (5) | C31—C30—C29 | 119.2 (5) |
C12—C13—H13A | 120.0 | C31—C30—H30A | 120.4 |
C14—C13—H13A | 120.0 | C29—C30—H30A | 120.4 |
O2—C14—C15 | 123.4 (5) | C30—C31—O4 | 125.4 (4) |
O2—C14—C13 | 116.7 (5) | C30—C31—C32 | 120.7 (4) |
C15—C14—C13 | 119.8 (4) | O4—C31—C32 | 114.0 (4) |
C14—C15—C16 | 118.5 (5) | C33—C32—C31 | 119.5 (5) |
C14—C15—H15A | 120.7 | C33—C32—H32A | 120.2 |
C16—C15—H15A | 120.7 | C31—C32—H32A | 120.2 |
C11—C16—C15 | 122.6 (5) | C32—C33—C28 | 121.3 (4) |
C11—C16—H16A | 118.7 | C32—C33—H33A | 119.4 |
C15—C16—H16A | 118.7 | C28—C33—H33A | 119.4 |
O2—C17—H17A | 109.5 | O4—C34—H34A | 109.5 |
O2—C17—H17B | 109.5 | O4—C34—H34B | 109.5 |
H17A—C17—H17B | 109.5 | H34A—C34—H34B | 109.5 |
O2—C17—H17C | 109.5 | O4—C34—H34C | 109.5 |
H17A—C17—H17C | 109.5 | H34A—C34—H34C | 109.5 |
H17B—C17—H17C | 109.5 | H34B—C34—H34C | 109.5 |
C8—N1—N2—C10 | −1.7 (6) | C25—N3—N4—C27 | −2.3 (5) |
C8—N1—N2—C5 | −169.9 (4) | C25—N3—N4—C22 | 175.2 (4) |
C7—C2—C3—C4 | 0.6 (7) | C24—C19—C20—C21 | −1.4 (7) |
C1—C2—C3—C4 | 176.4 (4) | C18—C19—C20—C21 | 178.9 (5) |
C2—C3—C4—C5 | −0.4 (7) | C19—C20—C21—C22 | 0.1 (7) |
C3—C4—C5—C6 | 1.5 (7) | C20—C21—C22—C23 | 0.8 (7) |
C3—C4—C5—N2 | −176.4 (4) | C20—C21—C22—N4 | −177.1 (4) |
C10—N2—C5—C4 | −45.2 (7) | C27—N4—C22—C21 | 42.1 (7) |
N1—N2—C5—C4 | 120.3 (5) | N3—N4—C22—C21 | −134.9 (4) |
C10—N2—C5—C6 | 136.8 (5) | C27—N4—C22—C23 | −135.7 (5) |
N1—N2—C5—C6 | −57.7 (6) | N3—N4—C22—C23 | 47.2 (6) |
C4—C5—C6—C7 | −2.7 (7) | C21—C22—C23—C24 | −0.4 (7) |
N2—C5—C6—C7 | 175.3 (4) | N4—C22—C23—C24 | 177.5 (4) |
C3—C2—C7—C6 | −2.0 (7) | C22—C23—C24—C19 | −1.0 (8) |
C1—C2—C7—C6 | −177.5 (5) | C20—C19—C24—C23 | 1.8 (7) |
C5—C6—C7—C2 | 3.0 (7) | C18—C19—C24—C23 | −178.5 (5) |
N2—N1—C8—O1 | 179.6 (5) | N4—N3—C25—O3 | 178.5 (4) |
N2—N1—C8—C9 | 1.7 (6) | N4—N3—C25—C26 | 3.1 (5) |
N1—C8—C9—C10 | −1.0 (7) | O3—C25—C26—C27 | −178.1 (5) |
O1—C8—C9—C10 | −178.9 (5) | N3—C25—C26—C27 | −2.9 (6) |
N1—N2—C10—C9 | 1.1 (6) | C25—C26—C27—N4 | 1.4 (6) |
C5—N2—C10—C9 | 167.2 (5) | C25—C26—C27—C28 | 179.2 (5) |
N1—N2—C10—C11 | 178.4 (4) | N3—N4—C27—C26 | 0.5 (5) |
C5—N2—C10—C11 | −15.4 (8) | C22—N4—C27—C26 | −176.6 (4) |
C8—C9—C10—N2 | −0.1 (6) | N3—N4—C27—C28 | −177.5 (4) |
C8—C9—C10—C11 | −177.2 (5) | C22—N4—C27—C28 | 5.3 (7) |
N2—C10—C11—C16 | −38.6 (8) | C26—C27—C28—C29 | 50.0 (7) |
C9—C10—C11—C16 | 138.1 (6) | N4—C27—C28—C29 | −132.4 (5) |
N2—C10—C11—C12 | 142.9 (5) | C26—C27—C28—C33 | −129.5 (6) |
C9—C10—C11—C12 | −40.4 (8) | N4—C27—C28—C33 | 48.1 (7) |
C16—C11—C12—C13 | −2.2 (8) | C33—C28—C29—C30 | −1.1 (7) |
C10—C11—C12—C13 | 176.3 (5) | C27—C28—C29—C30 | 179.4 (5) |
C11—C12—C13—C14 | 3.2 (8) | C28—C29—C30—C31 | 0.7 (8) |
C17—O2—C14—C15 | −13.9 (8) | C29—C30—C31—O4 | −179.7 (4) |
C17—O2—C14—C13 | 163.2 (5) | C29—C30—C31—C32 | 0.1 (7) |
C12—C13—C14—O2 | 179.5 (5) | C34—O4—C31—C30 | −6.1 (7) |
C12—C13—C14—C15 | −3.4 (8) | C34—O4—C31—C32 | 174.2 (4) |
O2—C14—C15—C16 | 179.5 (5) | C30—C31—C32—C33 | −0.5 (7) |
C13—C14—C15—C16 | 2.6 (8) | O4—C31—C32—C33 | 179.3 (4) |
C12—C11—C16—C15 | 1.5 (8) | C31—C32—C33—C28 | 0.1 (7) |
C10—C11—C16—C15 | −177.0 (5) | C29—C28—C33—C32 | 0.6 (7) |
C14—C15—C16—C11 | −1.7 (9) | C27—C28—C33—C32 | −179.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1E···N1i | 0.85 | 1.88 | 2.702 (5) | 164 |
O3—H3C···N3ii | 0.82 | 1.91 | 2.728 (5) | 175 |
C18—H18B···O1i | 0.96 | 2.50 | 3.380 (7) | 152 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H16N2O2 |
Mr | 280.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.2520 (19), 10.160 (2), 16.338 (3) |
α, β, γ (°) | 90.72 (3), 91.97 (3), 107.34 (3) |
V (Å3) | 1464.7 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.975, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6130, 5754, 2899 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.225, 1.09 |
No. of reflections | 5754 |
No. of parameters | 379 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.28 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1985), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1E···N1i | 0.85 | 1.880 | 2.702 (5) | 164.00 |
O3—H3C···N3ii | 0.82 | 1.910 | 2.728 (5) | 175.00 |
C18—H18B···O1i | 0.96 | 2.500 | 3.380 (7) | 152.00 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z. |
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In the process of synthesis, we obtained the title compound, (I), and we herein report its crystal structure.
The asymmetric unit of the title compound, (I), contains two crystallographically independent molecules, with methylphenyl and methoxyphenyl substituents in different orientations with respect to the pyrazole ring (Fig. 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987).
The rings A (N1/N2/C8—C10), B (C2—C7), C (C11—C16) and A' (N3/N4/C25—C27), B' (C19—C24), C' (C28—C33) are, of course, planar and they are oriented at diheral angles of A/B = 53.93 (2)°, A/C = 39.63 (3)°, B/C = 64.37 (2)° and A'/B' = 45.45 (2)°, A'/C' = 48.66 (3)°, B'/C' = 51.98 (3)°.
In the crystal structure, intermolecular O—H···N and C—H···O hydrogen bonds (Table 1) link the molecules, in which O—H···N bonds generate the centrosymmetric dimers, and they are connected by C—H···O bonds to generate one-dimensional double-stranded chains (Fig. 2).