organic compounds
3-(4-Bromophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
aEberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and bUniversity Mainz, Institut of Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: stefan.laufer@uni-tuebingen.de
The 16H11BrN2O, contains two independent molecules with slightly different geometries. The 4-bromobenzene ring forms dihedral angles of 26.0 (2) and 39.9 (7)° with the pyrazole ring in the two molecules while the phenyl ring is oriented at 19.7 (5) and 7.3 (0)° with respect to the pyrazole ring.
of the title compound, CRelated literature
For the biological activity of inhibitors for the microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO), see: Elkady et al. (2012). For details of the synthesis, see: Rathelot et al. (2002).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2010); cell X-AREA; data reduction: X-RED (Stoe & Cie, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.
Supporting information
10.1107/S1600536812046752/bt6856sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046752/bt6856Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812046752/bt6856Isup3.cml
The compound was prepared by a Vilsmeyer–Haack reaction. Phosphoryl chloride (4.16 ml, 44.7 mmol) was added dropwise to ice-cooled solution of 7 ml dimethylformamide. The mixture was left stirring for 30 min at 273 K. 4.3 g (14.9 mmol) of (E)-1-(1-(4-bromophenyl)ethylidene)-2-phenylhydrazine were dissolved in 10 ml dimethylformamide, and then slowly added to the mixture. The mixture was heated to 343 K and left for stirring for 4 h. The mixture was cooled to 273 K, quenched by water and adjusted to pH 12 with aqueous saturated sodium carbonate solution. The product was extracted with ethyl acetate three times, dried over anhydrous sodium sulfate and finally concentrated under vacuum. The product was purified by washing with methanol. Crystals of the title compound were obtained by slow evaporation of methanol at room temperature.
Hydrogen atoms were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.99–1.00 Å (sp3 C-atom). All H atoms were refined with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq of the parent atom).
Data collection: X-AREA (Stoe & Cie, 2010); cell
X-AREA (Stoe & Cie, 2010); data reduction: X-RED (Stoe & Cie, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. View of compound I. Displacement ellipsoids are drawn at the 50% probability level. |
C16H11BrN2O | Z = 4 |
Mr = 327.18 | F(000) = 656 |
Triclinic, P1 | Dx = 1.555 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6716 (8) Å | Cell parameters from 5561 reflections |
b = 11.4617 (9) Å | θ = 2.7–28.0° |
c = 13.8257 (10) Å | µ = 2.94 mm−1 |
α = 113.497 (5)° | T = 298 K |
β = 92.753 (6)° | Block, colourless |
γ = 93.753 (6)° | 0.34 × 0.18 × 0.06 mm |
V = 1397.91 (19) Å3 |
Stoe IPDS 2T diffractometer | 6740 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2856 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.0°, θmin = 2.6° |
rotation method scans | h = −12→11 |
Absorption correction: multi-scan (MULABS; Blessing, 1995) | k = −15→15 |
Tmin = 0.477, Tmax = 0.660 | l = −18→18 |
14312 measured reflections |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0707P)2] where P = (Fo2 + 2Fc2)/3 |
6740 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
C16H11BrN2O | γ = 93.753 (6)° |
Mr = 327.18 | V = 1397.91 (19) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.6716 (8) Å | Mo Kα radiation |
b = 11.4617 (9) Å | µ = 2.94 mm−1 |
c = 13.8257 (10) Å | T = 298 K |
α = 113.497 (5)° | 0.34 × 0.18 × 0.06 mm |
β = 92.753 (6)° |
Stoe IPDS 2T diffractometer | 6740 independent reflections |
Absorption correction: multi-scan (MULABS; Blessing, 1995) | 2856 reflections with I > 2σ(I) |
Tmin = 0.477, Tmax = 0.660 | Rint = 0.063 |
14312 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.52 e Å−3 |
6740 reflections | Δρmin = −0.73 e Å−3 |
361 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 | 0.32448 (7) | 0.17418 (5) | −0.10411 (4) | 0.0974 (3) | |
N1 | 0.2200 (3) | 0.6242 (3) | 0.3849 (2) | 0.0482 (8) | |
N2 | 0.2418 (3) | 0.7380 (3) | 0.4705 (2) | 0.0456 (7) | |
C3 | 0.3427 (4) | 0.8149 (3) | 0.4591 (3) | 0.0468 (9) | |
H3 | 0.3743 | 0.8967 | 0.5078 | 0.056* | |
C4 | 0.3921 (4) | 0.7507 (3) | 0.3612 (3) | 0.0456 (9) | |
C5 | 0.3115 (4) | 0.6312 (3) | 0.3181 (3) | 0.0457 (9) | |
C6 | 0.1618 (4) | 0.7599 (3) | 0.5587 (3) | 0.0450 (9) | |
C7 | 0.1515 (4) | 0.8810 (4) | 0.6313 (3) | 0.0570 (10) | |
H7 | 0.1947 | 0.9507 | 0.6226 | 0.068* | |
C8 | 0.0763 (5) | 0.8990 (4) | 0.7178 (3) | 0.0660 (12) | |
H8 | 0.0710 | 0.9814 | 0.7683 | 0.079* | |
C9 | 0.0099 (5) | 0.7980 (4) | 0.7302 (4) | 0.0692 (12) | |
H9 | −0.0417 | 0.8110 | 0.7881 | 0.083* | |
C10 | 0.0202 (5) | 0.6772 (4) | 0.6565 (4) | 0.0703 (13) | |
H10 | −0.0256 | 0.6078 | 0.6641 | 0.084* | |
C11 | 0.0976 (4) | 0.6567 (4) | 0.5708 (3) | 0.0579 (11) | |
H11 | 0.1061 | 0.5741 | 0.5219 | 0.070* | |
C12 | 0.5114 (4) | 0.7921 (4) | 0.3201 (3) | 0.0537 (10) | |
H12 | 0.5384 | 0.7351 | 0.2559 | 0.064* | |
O13 | 0.5781 (3) | 0.8928 (3) | 0.3614 (2) | 0.0668 (8) | |
C14 | 0.3153 (4) | 0.5230 (4) | 0.2171 (3) | 0.0456 (9) | |
C15 | 0.3337 (4) | 0.5387 (4) | 0.1243 (3) | 0.0556 (10) | |
H15 | 0.3454 | 0.6209 | 0.1264 | 0.067* | |
C16 | 0.3352 (4) | 0.4363 (4) | 0.0292 (3) | 0.0626 (11) | |
H16 | 0.3460 | 0.4488 | −0.0326 | 0.075* | |
C17 | 0.3207 (4) | 0.3157 (4) | 0.0265 (3) | 0.0610 (11) | |
C18 | 0.3015 (4) | 0.2953 (4) | 0.1167 (3) | 0.0583 (11) | |
H18 | 0.2904 | 0.2128 | 0.1139 | 0.070* | |
C19 | 0.2991 (4) | 0.3994 (4) | 0.2112 (3) | 0.0524 (10) | |
H19 | 0.2863 | 0.3863 | 0.2725 | 0.063* | |
Br2 | 0.83318 (7) | 0.15393 (6) | −0.08996 (5) | 0.1091 (3) | |
N21 | 0.7249 (3) | 0.6207 (3) | 0.3891 (2) | 0.0473 (8) | |
N22 | 0.7455 (3) | 0.7353 (3) | 0.4734 (2) | 0.0453 (7) | |
C23 | 0.8472 (4) | 0.8114 (3) | 0.4605 (3) | 0.0487 (9) | |
H23 | 0.8795 | 0.8934 | 0.5084 | 0.058* | |
C24 | 0.8949 (4) | 0.7456 (3) | 0.3631 (3) | 0.0478 (9) | |
C25 | 0.8145 (4) | 0.6255 (3) | 0.3209 (3) | 0.0457 (9) | |
C26 | 0.6588 (4) | 0.7623 (4) | 0.5591 (3) | 0.0484 (9) | |
C27 | 0.6652 (5) | 0.8807 (4) | 0.6382 (3) | 0.0638 (12) | |
H27 | 0.7294 | 0.9451 | 0.6390 | 0.077* | |
C28 | 0.5759 (5) | 0.9050 (4) | 0.7174 (4) | 0.0692 (12) | |
H28 | 0.5813 | 0.9858 | 0.7721 | 0.083* | |
C29 | 0.4796 (5) | 0.8119 (4) | 0.7167 (3) | 0.0623 (11) | |
H29 | 0.4192 | 0.8288 | 0.7700 | 0.075* | |
C30 | 0.4738 (4) | 0.6930 (4) | 0.6357 (4) | 0.0620 (11) | |
H30 | 0.4084 | 0.6289 | 0.6342 | 0.074* | |
C31 | 0.5632 (4) | 0.6669 (4) | 0.5567 (3) | 0.0553 (10) | |
H31 | 0.5589 | 0.5858 | 0.5024 | 0.066* | |
C32 | 0.9995 (4) | 0.7970 (4) | 0.3158 (3) | 0.0593 (11) | |
H32 | 1.0124 | 0.7504 | 0.2449 | 0.071* | |
O33 | 1.0705 (3) | 0.8950 (3) | 0.3615 (3) | 0.0702 (9) | |
C34 | 0.8187 (4) | 0.5151 (3) | 0.2220 (3) | 0.0477 (9) | |
C35 | 0.9388 (4) | 0.4886 (4) | 0.1687 (3) | 0.0595 (11) | |
H35 | 1.0188 | 0.5443 | 0.1966 | 0.071* | |
C36 | 0.9428 (4) | 0.3834 (4) | 0.0769 (4) | 0.0657 (12) | |
H36 | 1.0239 | 0.3691 | 0.0420 | 0.079* | |
C37 | 0.8276 (5) | 0.2994 (4) | 0.0365 (3) | 0.0630 (11) | |
C38 | 0.7060 (5) | 0.3220 (4) | 0.0872 (3) | 0.0623 (11) | |
H38 | 0.6271 | 0.2647 | 0.0595 | 0.075* | |
C39 | 0.7026 (4) | 0.4291 (4) | 0.1782 (3) | 0.0543 (10) | |
H39 | 0.6202 | 0.4446 | 0.2114 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1105 (5) | 0.0877 (4) | 0.0613 (3) | −0.0126 (3) | 0.0273 (3) | −0.0034 (3) |
N1 | 0.0435 (19) | 0.0514 (17) | 0.0455 (17) | −0.0017 (14) | 0.0070 (14) | 0.0157 (15) |
N2 | 0.0432 (19) | 0.0482 (17) | 0.0444 (17) | −0.0026 (14) | 0.0089 (14) | 0.0180 (15) |
C3 | 0.045 (2) | 0.0484 (19) | 0.047 (2) | −0.0034 (17) | 0.0084 (17) | 0.0208 (18) |
C4 | 0.040 (2) | 0.051 (2) | 0.046 (2) | −0.0008 (16) | 0.0083 (17) | 0.0208 (18) |
C5 | 0.038 (2) | 0.055 (2) | 0.045 (2) | 0.0029 (17) | 0.0066 (17) | 0.0212 (18) |
C6 | 0.041 (2) | 0.055 (2) | 0.041 (2) | 0.0006 (17) | 0.0086 (16) | 0.0219 (18) |
C7 | 0.059 (3) | 0.054 (2) | 0.057 (2) | −0.0005 (19) | 0.015 (2) | 0.021 (2) |
C8 | 0.065 (3) | 0.063 (3) | 0.058 (3) | 0.004 (2) | 0.018 (2) | 0.010 (2) |
C9 | 0.068 (3) | 0.080 (3) | 0.054 (3) | −0.002 (2) | 0.023 (2) | 0.021 (2) |
C10 | 0.076 (3) | 0.073 (3) | 0.066 (3) | −0.007 (2) | 0.024 (2) | 0.033 (3) |
C11 | 0.062 (3) | 0.055 (2) | 0.054 (2) | 0.002 (2) | 0.015 (2) | 0.018 (2) |
C12 | 0.053 (3) | 0.062 (2) | 0.052 (2) | 0.003 (2) | 0.0122 (19) | 0.028 (2) |
O13 | 0.0653 (19) | 0.0557 (16) | 0.075 (2) | −0.0154 (14) | 0.0153 (16) | 0.0234 (15) |
C14 | 0.034 (2) | 0.060 (2) | 0.043 (2) | 0.0019 (17) | 0.0079 (16) | 0.0206 (18) |
C15 | 0.057 (3) | 0.059 (2) | 0.053 (2) | −0.0051 (19) | 0.0065 (19) | 0.026 (2) |
C16 | 0.062 (3) | 0.077 (3) | 0.046 (2) | −0.011 (2) | 0.006 (2) | 0.024 (2) |
C17 | 0.053 (3) | 0.068 (3) | 0.047 (2) | −0.006 (2) | 0.0162 (19) | 0.007 (2) |
C18 | 0.055 (3) | 0.050 (2) | 0.064 (3) | 0.0037 (18) | 0.016 (2) | 0.016 (2) |
C19 | 0.052 (2) | 0.056 (2) | 0.051 (2) | 0.0059 (18) | 0.0121 (18) | 0.0232 (19) |
Br2 | 0.1057 (5) | 0.0904 (4) | 0.0834 (4) | −0.0047 (3) | 0.0324 (4) | −0.0156 (3) |
N21 | 0.0460 (19) | 0.0457 (16) | 0.0471 (18) | −0.0029 (14) | 0.0079 (15) | 0.0162 (15) |
N22 | 0.0445 (19) | 0.0414 (15) | 0.0457 (17) | −0.0028 (13) | 0.0053 (14) | 0.0138 (14) |
C23 | 0.046 (2) | 0.0447 (19) | 0.052 (2) | −0.0031 (17) | 0.0096 (18) | 0.0164 (18) |
C24 | 0.043 (2) | 0.049 (2) | 0.051 (2) | −0.0016 (17) | 0.0074 (18) | 0.0198 (18) |
C25 | 0.040 (2) | 0.049 (2) | 0.046 (2) | −0.0013 (16) | 0.0015 (17) | 0.0177 (18) |
C26 | 0.047 (2) | 0.052 (2) | 0.048 (2) | 0.0028 (17) | 0.0075 (18) | 0.0221 (19) |
C27 | 0.063 (3) | 0.055 (2) | 0.061 (3) | −0.007 (2) | 0.012 (2) | 0.012 (2) |
C28 | 0.069 (3) | 0.067 (3) | 0.059 (3) | 0.006 (2) | 0.017 (2) | 0.010 (2) |
C29 | 0.056 (3) | 0.082 (3) | 0.055 (3) | 0.011 (2) | 0.017 (2) | 0.031 (2) |
C30 | 0.058 (3) | 0.066 (3) | 0.066 (3) | −0.004 (2) | 0.013 (2) | 0.031 (2) |
C31 | 0.056 (3) | 0.052 (2) | 0.055 (2) | −0.0034 (19) | 0.011 (2) | 0.0189 (19) |
C32 | 0.064 (3) | 0.053 (2) | 0.062 (3) | 0.001 (2) | 0.020 (2) | 0.023 (2) |
O33 | 0.0640 (19) | 0.0537 (16) | 0.088 (2) | −0.0133 (14) | 0.0199 (16) | 0.0247 (16) |
C34 | 0.041 (2) | 0.055 (2) | 0.049 (2) | 0.0007 (17) | 0.0062 (17) | 0.0231 (19) |
C35 | 0.040 (2) | 0.063 (2) | 0.062 (3) | −0.0044 (18) | 0.0065 (19) | 0.012 (2) |
C36 | 0.043 (2) | 0.072 (3) | 0.070 (3) | 0.004 (2) | 0.020 (2) | 0.015 (2) |
C37 | 0.066 (3) | 0.060 (2) | 0.052 (2) | 0.004 (2) | 0.018 (2) | 0.009 (2) |
C38 | 0.053 (3) | 0.064 (2) | 0.057 (3) | −0.011 (2) | 0.006 (2) | 0.013 (2) |
C39 | 0.043 (2) | 0.062 (2) | 0.052 (2) | −0.0064 (18) | 0.0100 (18) | 0.018 (2) |
Br1—C17 | 1.890 (4) | Br2—C37 | 1.880 (4) |
N1—C5 | 1.330 (4) | N21—C25 | 1.326 (4) |
N1—N2 | 1.363 (4) | N21—N22 | 1.358 (4) |
N2—C3 | 1.330 (4) | N22—C23 | 1.337 (4) |
N2—C6 | 1.421 (4) | N22—C26 | 1.428 (5) |
C3—C4 | 1.383 (5) | C23—C24 | 1.375 (5) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.416 (5) | C24—C25 | 1.420 (5) |
C4—C12 | 1.445 (5) | C24—C32 | 1.446 (5) |
C5—C14 | 1.457 (5) | C25—C34 | 1.451 (5) |
C6—C7 | 1.364 (5) | C26—C27 | 1.357 (6) |
C6—C11 | 1.372 (5) | C26—C31 | 1.374 (5) |
C7—C8 | 1.382 (6) | C27—C28 | 1.379 (6) |
C7—H7 | 0.9300 | C27—H27 | 0.9300 |
C8—C9 | 1.362 (6) | C28—C29 | 1.366 (6) |
C8—H8 | 0.9300 | C28—H28 | 0.9300 |
C9—C10 | 1.367 (6) | C29—C30 | 1.371 (6) |
C9—H9 | 0.9300 | C29—H29 | 0.9300 |
C10—C11 | 1.381 (5) | C30—C31 | 1.377 (5) |
C10—H10 | 0.9300 | C30—H30 | 0.9300 |
C11—H11 | 0.9300 | C31—H31 | 0.9300 |
C12—O13 | 1.190 (4) | C32—O33 | 1.193 (5) |
C12—H12 | 0.9300 | C32—H32 | 0.9300 |
C14—C15 | 1.383 (5) | C34—C39 | 1.383 (5) |
C14—C19 | 1.384 (5) | C34—C35 | 1.391 (5) |
C15—C16 | 1.371 (6) | C35—C36 | 1.363 (6) |
C15—H15 | 0.9300 | C35—H35 | 0.9300 |
C16—C17 | 1.365 (6) | C36—C37 | 1.361 (6) |
C16—H16 | 0.9300 | C36—H36 | 0.9300 |
C17—C18 | 1.377 (6) | C37—C38 | 1.384 (6) |
C18—C19 | 1.376 (5) | C38—C39 | 1.368 (5) |
C18—H18 | 0.9300 | C38—H38 | 0.9300 |
C19—H19 | 0.9300 | C39—H39 | 0.9300 |
C5—N1—N2 | 105.3 (3) | C25—N21—N22 | 106.1 (3) |
C3—N2—N1 | 112.2 (3) | C23—N22—N21 | 111.8 (3) |
C3—N2—C6 | 128.4 (3) | C23—N22—C26 | 128.6 (3) |
N1—N2—C6 | 119.4 (3) | N21—N22—C26 | 119.6 (3) |
N2—C3—C4 | 107.3 (3) | N22—C23—C24 | 107.1 (3) |
N2—C3—H3 | 126.4 | N22—C23—H23 | 126.5 |
C4—C3—H3 | 126.4 | C24—C23—H23 | 126.5 |
C3—C4—C5 | 104.7 (3) | C23—C24—C25 | 105.3 (3) |
C3—C4—C12 | 126.5 (3) | C23—C24—C32 | 124.8 (3) |
C5—C4—C12 | 128.3 (3) | C25—C24—C32 | 129.8 (3) |
N1—C5—C4 | 110.5 (3) | N21—C25—C24 | 109.7 (3) |
N1—C5—C14 | 119.1 (3) | N21—C25—C34 | 119.2 (3) |
C4—C5—C14 | 130.3 (3) | C24—C25—C34 | 131.1 (3) |
C7—C6—C11 | 120.5 (3) | C27—C26—C31 | 120.5 (4) |
C7—C6—N2 | 120.7 (3) | C27—C26—N22 | 121.2 (3) |
C11—C6—N2 | 118.8 (3) | C31—C26—N22 | 118.2 (3) |
C6—C7—C8 | 119.4 (4) | C26—C27—C28 | 119.7 (4) |
C6—C7—H7 | 120.3 | C26—C27—H27 | 120.2 |
C8—C7—H7 | 120.3 | C28—C27—H27 | 120.2 |
C9—C8—C7 | 120.9 (4) | C29—C28—C27 | 120.9 (4) |
C9—C8—H8 | 119.5 | C29—C28—H28 | 119.5 |
C7—C8—H8 | 119.5 | C27—C28—H28 | 119.5 |
C8—C9—C10 | 119.1 (4) | C28—C29—C30 | 118.7 (4) |
C8—C9—H9 | 120.4 | C28—C29—H29 | 120.6 |
C10—C9—H9 | 120.4 | C30—C29—H29 | 120.6 |
C9—C10—C11 | 120.9 (4) | C29—C30—C31 | 121.0 (4) |
C9—C10—H10 | 119.5 | C29—C30—H30 | 119.5 |
C11—C10—H10 | 119.5 | C31—C30—H30 | 119.5 |
C6—C11—C10 | 119.1 (4) | C26—C31—C30 | 119.1 (4) |
C6—C11—H11 | 120.4 | C26—C31—H31 | 120.4 |
C10—C11—H11 | 120.4 | C30—C31—H31 | 120.4 |
O13—C12—C4 | 125.6 (4) | O33—C32—C24 | 124.6 (4) |
O13—C12—H12 | 117.2 | O33—C32—H32 | 117.7 |
C4—C12—H12 | 117.2 | C24—C32—H32 | 117.7 |
C15—C14—C19 | 117.7 (4) | C39—C34—C35 | 117.1 (4) |
C15—C14—C5 | 122.1 (3) | C39—C34—C25 | 120.7 (3) |
C19—C14—C5 | 120.3 (3) | C35—C34—C25 | 122.2 (3) |
C16—C15—C14 | 121.7 (4) | C36—C35—C34 | 122.0 (4) |
C16—C15—H15 | 119.2 | C36—C35—H35 | 119.0 |
C14—C15—H15 | 119.2 | C34—C35—H35 | 119.0 |
C17—C16—C15 | 119.1 (4) | C37—C36—C35 | 119.7 (4) |
C17—C16—H16 | 120.5 | C37—C36—H36 | 120.2 |
C15—C16—H16 | 120.5 | C35—C36—H36 | 120.2 |
C16—C17—C18 | 121.3 (4) | C36—C37—C38 | 120.2 (4) |
C16—C17—Br1 | 119.3 (3) | C36—C37—Br2 | 119.7 (3) |
C18—C17—Br1 | 119.4 (3) | C38—C37—Br2 | 120.1 (3) |
C19—C18—C17 | 118.7 (4) | C39—C38—C37 | 119.5 (4) |
C19—C18—H18 | 120.6 | C39—C38—H38 | 120.2 |
C17—C18—H18 | 120.6 | C37—C38—H38 | 120.2 |
C18—C19—C14 | 121.5 (4) | C38—C39—C34 | 121.5 (4) |
C18—C19—H19 | 119.2 | C38—C39—H39 | 119.2 |
C14—C19—H19 | 119.2 | C34—C39—H39 | 119.2 |
C5—N1—N2—C3 | 0.2 (4) | C25—N21—N22—C23 | −0.8 (4) |
C5—N1—N2—C6 | −178.3 (3) | C25—N21—N22—C26 | 176.9 (3) |
N1—N2—C3—C4 | −0.0 (4) | N21—N22—C23—C24 | 0.8 (4) |
C6—N2—C3—C4 | 178.3 (4) | C26—N22—C23—C24 | −176.6 (4) |
N2—C3—C4—C5 | −0.1 (4) | N22—C23—C24—C25 | −0.5 (4) |
N2—C3—C4—C12 | −173.0 (4) | N22—C23—C24—C32 | 176.1 (4) |
N2—N1—C5—C4 | −0.3 (4) | N22—N21—C25—C24 | 0.5 (4) |
N2—N1—C5—C14 | 180.0 (3) | N22—N21—C25—C34 | 179.3 (3) |
C3—C4—C5—N1 | 0.3 (4) | C23—C24—C25—N21 | −0.0 (5) |
C12—C4—C5—N1 | 172.9 (4) | C32—C24—C25—N21 | −176.4 (4) |
C3—C4—C5—C14 | 180.0 (4) | C23—C24—C25—C34 | −178.6 (4) |
C12—C4—C5—C14 | −7.4 (7) | C32—C24—C25—C34 | 5.0 (7) |
C3—N2—C6—C7 | 20.3 (6) | C23—N22—C26—C27 | 5.3 (6) |
N1—N2—C6—C7 | −161.4 (4) | N21—N22—C26—C27 | −171.9 (4) |
C3—N2—C6—C11 | −158.2 (4) | C23—N22—C26—C31 | −178.0 (4) |
N1—N2—C6—C11 | 20.0 (5) | N21—N22—C26—C31 | 4.7 (5) |
C11—C6—C7—C8 | 0.4 (7) | C31—C26—C27—C28 | 0.7 (7) |
N2—C6—C7—C8 | −178.1 (4) | N22—C26—C27—C28 | 177.3 (4) |
C6—C7—C8—C9 | −1.5 (7) | C26—C27—C28—C29 | −0.9 (8) |
C7—C8—C9—C10 | 1.0 (8) | C27—C28—C29—C30 | 0.4 (7) |
C8—C9—C10—C11 | 0.6 (8) | C28—C29—C30—C31 | 0.3 (7) |
C7—C6—C11—C10 | 1.1 (7) | C27—C26—C31—C30 | −0.0 (7) |
N2—C6—C11—C10 | 179.7 (4) | N22—C26—C31—C30 | −176.7 (4) |
C9—C10—C11—C6 | −1.7 (7) | C29—C30—C31—C26 | −0.5 (7) |
C3—C4—C12—O13 | −6.5 (7) | C23—C24—C32—O33 | 11.3 (7) |
C5—C4—C12—O13 | −177.6 (4) | C25—C24—C32—O33 | −172.9 (4) |
N1—C5—C14—C15 | 139.7 (4) | N21—C25—C34—C39 | 26.1 (6) |
C4—C5—C14—C15 | −40.0 (6) | C24—C25—C34—C39 | −155.4 (4) |
N1—C5—C14—C19 | −39.7 (5) | N21—C25—C34—C35 | −152.2 (4) |
C4—C5—C14—C19 | 140.6 (4) | C24—C25—C34—C35 | 26.3 (7) |
C19—C14—C15—C16 | 0.4 (6) | C39—C34—C35—C36 | 0.5 (6) |
C5—C14—C15—C16 | −179.0 (4) | C25—C34—C35—C36 | 178.8 (4) |
C14—C15—C16—C17 | −1.2 (7) | C34—C35—C36—C37 | −1.6 (7) |
C15—C16—C17—C18 | 1.5 (7) | C35—C36—C37—C38 | 1.4 (7) |
C15—C16—C17—Br1 | −179.4 (3) | C35—C36—C37—Br2 | −179.8 (4) |
C16—C17—C18—C19 | −1.0 (7) | C36—C37—C38—C39 | −0.2 (7) |
Br1—C17—C18—C19 | 180.0 (3) | Br2—C37—C38—C39 | −179.0 (3) |
C17—C18—C19—C14 | 0.1 (6) | C37—C38—C39—C34 | −1.0 (7) |
C15—C14—C19—C18 | 0.2 (6) | C35—C34—C39—C38 | 0.8 (6) |
C5—C14—C19—C18 | 179.6 (4) | C25—C34—C39—C38 | −177.5 (4) |
Experimental details
Crystal data | |
Chemical formula | C16H11BrN2O |
Mr | 327.18 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.6716 (8), 11.4617 (9), 13.8257 (10) |
α, β, γ (°) | 113.497 (5), 92.753 (6), 93.753 (6) |
V (Å3) | 1397.91 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.94 |
Crystal size (mm) | 0.34 × 0.18 × 0.06 |
Data collection | |
Diffractometer | Stoe IPDS 2T diffractometer |
Absorption correction | Multi-scan (MULABS; Blessing, 1995) |
Tmin, Tmax | 0.477, 0.660 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14312, 6740, 2856 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.158, 0.92 |
No. of reflections | 6740 |
No. of parameters | 361 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.73 |
Computer programs: X-AREA (Stoe & Cie, 2010), X-RED (Stoe & Cie, 2010), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
Acknowledgements
This research was supported financially by the Landesgraduiertenförderung program of the Ministry of Science, Research and Arts of the state of Baden-Württemberg, Germany.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
We synthesized and evaluated inhibitors for the microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO) (Elkady et al., 2012). The title compound was synthesized to obtain a template which leads to series of different derivates of the pyrazole scaffold (Rathelot et al., 2002) the asymmetric unit of the crystal structure contains two slightly different molecules.
The 4-Bromobenzene ring is oriented with dihedral angles of 26.0 (2)°, 39.9 (7)° (first and second molecule) with the pyrazole ring. The phenyl ring is oriented with dihedral angles of 19.7 (5)°, 7.3 (0)° with the pyrazole ring.