Acta Cryst. (2010). E66, o2961 [ doi:10.1107/S1600536810040158 ]
In the title compound, C17H14BrClN4O2, the pyrazole ring is almost coplanar with the benzene ring [dihedral angle = 0.5 (2)°], whereas the pyrazole ring is close to perpendicular to the 3-chloropyridine ring [dihedral angle = 73.7 (2)°]. An intramolecular C-H
O hydrogen bond occurs. The dominant interaction in the crystal packing is an N-HN hydrogen bond, which generates a chain along the c axis. Weak intermolecular C-HO and C-HN contacts are also observed
Compound (I) was prepared according to the reported procedure of Dong et al.(2009). Colourless single crystals suitable for X-ray diffraction analysis were obtained by recrystallization from ethanol.
H atom of N—H was located in a difference map and refined freely. All C—H atoms were generated by riding model with C—H distance fixed at 0.93(phenyl group), 0.97(methylene group).
Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./kp2276fig1thm.gif)
| Fig. 1. The molecular structure of (I) with intramolecular C—H···O interaction, showing displacement ellipsoids drawn at the 30% probability level. |
![[Figure 2]](./kp2276fig2thm.gif)
| Fig. 2. The crystal packing of I with hydrogen bonds shown (in dashed lines). |
![[Figure 3]](./kp2276fig3thm.gif)
| Fig. 3. The formation of the title compound. |
| C17H14BrClN4O2 | F(000) = 848 |
| Mr = 421.68 | Dx = 1.654 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 4811 reflections |
| a = 16.821 (3) Å | θ = 2.0–27.1° |
| b = 10.195 (2) Å | µ = 2.60 mm−1 |
| c = 10.064 (2) Å | T = 113 K |
| β = 101.09 (3)° | Ractangle, colourless |
| V = 1693.7 (6) Å3 | 0.16 × 0.12 × 0.08 mm |
| Z = 4 |
| Rigaku Saturn diffractometer | 2967 independent reflections |
| Radiation source: rotating anode | 2459 reflections with I > 2σ(I) |
| confocal | Rint = 0.049 |
| ω scans | θmax = 25.0°, θmin = 2.4° |
| Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2002) | h = −14→20 |
| Tmin = 0.681, Tmax = 0.819 | k = −11→12 |
| 11217 measured reflections | l = −11→11 |
| 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
| S = 0.99 | w = 1/[σ2(Fo2) + (0.0325P)2] where P = (Fo2 + 2Fc2)/3 |
| 2967 reflections | (Δ/σ)max = 0.002 |
| 231 parameters | Δρmax = 0.44 e Å−3 |
| 1 restraint | Δρmin = −0.37 e Å−3 |
| C17H14BrClN4O2 | V = 1693.7 (6) Å3 |
| Mr = 421.68 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 16.821 (3) Å | µ = 2.60 mm−1 |
| b = 10.195 (2) Å | T = 113 K |
| c = 10.064 (2) Å | 0.16 × 0.12 × 0.08 mm |
| β = 101.09 (3)° |
| Rigaku Saturn diffractometer | 2459 reflections with I > 2σ(I) |
| Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2002) | Rint = 0.049 |
| Tmin = 0.681, Tmax = 0.819 | θmax = 25.0° |
| 11217 measured reflections | Standard reflections: 0 |
| 2967 independent reflections |
| R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.064 | Δρmax = 0.44 e Å−3 |
| S = 0.99 | Δρmin = −0.37 e Å−3 |
| 2967 reflections | Absolute structure: ? |
| 231 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
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 | 0.023579 (14) | 0.06344 (2) | 0.32526 (2) | 0.02098 (9) | |
| Cl1 | 0.07553 (4) | 0.63129 (7) | 0.54321 (6) | 0.02706 (17) | |
| O1 | 0.49241 (10) | 0.39661 (16) | 1.23908 (18) | 0.0251 (4) | |
| O2 | 0.25436 (9) | 0.48804 (16) | 0.66299 (16) | 0.0182 (4) | |
| N1 | 0.26429 (11) | 0.29027 (19) | 0.77115 (19) | 0.0143 (5) | |
| N2 | 0.09269 (10) | 0.31241 (18) | 0.35049 (19) | 0.0148 (5) | |
| N3 | 0.14508 (10) | 0.38461 (18) | 0.44293 (18) | 0.0125 (4) | |
| N4 | 0.21996 (11) | 0.49665 (19) | 0.3078 (2) | 0.0171 (5) | |
| C1 | 0.32339 (13) | 0.3197 (2) | 0.8882 (2) | 0.0147 (5) | |
| C2 | 0.34708 (16) | 0.4465 (2) | 0.9280 (3) | 0.0292 (7) | |
| H2 | 0.3250 | 0.5177 | 0.8759 | 0.035* | |
| C3 | 0.40344 (16) | 0.4662 (3) | 1.0450 (3) | 0.0318 (8) | |
| H3 | 0.4189 | 0.5514 | 1.0712 | 0.038* | |
| C4 | 0.43755 (13) | 0.3629 (2) | 1.1245 (2) | 0.0181 (6) | |
| C5 | 0.41491 (13) | 0.2361 (2) | 1.0851 (2) | 0.0162 (6) | |
| H5 | 0.4372 | 0.1650 | 1.1372 | 0.019* | |
| C6 | 0.35841 (13) | 0.2165 (2) | 0.9668 (2) | 0.0165 (6) | |
| H6 | 0.3437 | 0.1313 | 0.9398 | 0.020* | |
| C7 | 0.53387 (14) | 0.2914 (2) | 1.3173 (2) | 0.0204 (6) | |
| H7A | 0.5647 | 0.2407 | 1.2631 | 0.024* | |
| H7B | 0.4954 | 0.2336 | 1.3481 | 0.024* | |
| C8 | 0.58986 (14) | 0.3521 (3) | 1.4367 (3) | 0.0257 (7) | |
| H8A | 0.6282 | 0.4079 | 1.4048 | 0.039* | |
| H8B | 0.6182 | 0.2841 | 1.4925 | 0.039* | |
| H8C | 0.5588 | 0.4031 | 1.4886 | 0.039* | |
| C9 | 0.23427 (13) | 0.3734 (2) | 0.6695 (2) | 0.0128 (5) | |
| C10 | 0.17324 (13) | 0.3141 (2) | 0.5591 (2) | 0.0133 (5) | |
| C11 | 0.13590 (13) | 0.1945 (2) | 0.5421 (2) | 0.0141 (5) | |
| H11 | 0.1412 | 0.1253 | 0.6033 | 0.017* | |
| C12 | 0.08813 (13) | 0.1993 (2) | 0.4129 (2) | 0.0143 (5) | |
| C13 | 0.17110 (13) | 0.5071 (2) | 0.3970 (2) | 0.0144 (5) | |
| C14 | 0.14284 (13) | 0.6260 (2) | 0.4354 (2) | 0.0173 (6) | |
| C15 | 0.16840 (15) | 0.7398 (2) | 0.3811 (3) | 0.0247 (7) | |
| H15 | 0.1510 | 0.8214 | 0.4056 | 0.030* | |
| C16 | 0.21971 (15) | 0.7303 (2) | 0.2907 (3) | 0.0257 (7) | |
| H16 | 0.2381 | 0.8052 | 0.2532 | 0.031* | |
| C17 | 0.24346 (14) | 0.6071 (3) | 0.2566 (2) | 0.0226 (6) | |
| H17 | 0.2777 | 0.6011 | 0.1945 | 0.027* | |
| H1 | 0.2473 (12) | 0.2088 (11) | 0.765 (2) | 0.013 (6)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.02471 (15) | 0.01863 (15) | 0.01646 (15) | −0.00563 (10) | −0.00392 (10) | −0.00200 (11) |
| Cl1 | 0.0241 (3) | 0.0302 (4) | 0.0266 (4) | 0.0044 (3) | 0.0042 (3) | −0.0100 (3) |
| O1 | 0.0317 (10) | 0.0178 (10) | 0.0183 (10) | −0.0035 (7) | −0.0142 (8) | 0.0027 (8) |
| O2 | 0.0232 (9) | 0.0126 (9) | 0.0163 (9) | −0.0023 (7) | −0.0023 (7) | 0.0005 (7) |
| N1 | 0.0168 (10) | 0.0128 (11) | 0.0113 (11) | −0.0031 (8) | −0.0022 (8) | −0.0001 (9) |
| N2 | 0.0165 (10) | 0.0159 (11) | 0.0107 (11) | −0.0010 (8) | −0.0011 (8) | −0.0029 (9) |
| N3 | 0.0162 (10) | 0.0103 (10) | 0.0101 (10) | −0.0011 (8) | 0.0000 (8) | −0.0013 (8) |
| N4 | 0.0183 (11) | 0.0175 (12) | 0.0133 (11) | 0.0002 (9) | −0.0025 (8) | −0.0013 (9) |
| C1 | 0.0139 (12) | 0.0157 (13) | 0.0136 (13) | −0.0017 (10) | 0.0000 (10) | 0.0007 (10) |
| C2 | 0.0378 (16) | 0.0161 (15) | 0.0250 (16) | 0.0011 (11) | −0.0154 (12) | 0.0036 (12) |
| C3 | 0.0452 (18) | 0.0155 (14) | 0.0260 (16) | −0.0053 (12) | −0.0145 (13) | −0.0015 (12) |
| C4 | 0.0191 (13) | 0.0200 (14) | 0.0127 (13) | −0.0019 (10) | −0.0034 (10) | −0.0002 (11) |
| C5 | 0.0185 (13) | 0.0163 (13) | 0.0124 (14) | 0.0016 (10) | 0.0000 (10) | 0.0036 (10) |
| C6 | 0.0160 (12) | 0.0133 (13) | 0.0191 (15) | −0.0016 (9) | 0.0006 (10) | −0.0003 (10) |
| C7 | 0.0213 (13) | 0.0219 (14) | 0.0153 (14) | 0.0016 (10) | −0.0031 (11) | 0.0036 (11) |
| C8 | 0.0240 (14) | 0.0275 (16) | 0.0209 (15) | −0.0052 (11) | −0.0078 (11) | 0.0032 (12) |
| C9 | 0.0127 (12) | 0.0136 (13) | 0.0121 (13) | 0.0016 (10) | 0.0027 (9) | −0.0021 (10) |
| C10 | 0.0148 (12) | 0.0129 (13) | 0.0113 (13) | 0.0029 (9) | 0.0004 (10) | 0.0025 (10) |
| C11 | 0.0173 (13) | 0.0142 (13) | 0.0109 (13) | 0.0000 (10) | 0.0025 (10) | 0.0028 (10) |
| C12 | 0.0151 (12) | 0.0155 (14) | 0.0124 (13) | −0.0011 (10) | 0.0029 (10) | −0.0013 (10) |
| C13 | 0.0153 (12) | 0.0144 (13) | 0.0104 (13) | −0.0012 (10) | −0.0050 (10) | 0.0017 (10) |
| C14 | 0.0180 (13) | 0.0170 (13) | 0.0142 (13) | 0.0026 (10) | −0.0035 (10) | −0.0030 (11) |
| C15 | 0.0277 (15) | 0.0130 (13) | 0.0275 (17) | 0.0024 (11) | −0.0097 (12) | 0.0010 (12) |
| C16 | 0.0294 (15) | 0.0179 (15) | 0.0241 (16) | −0.0075 (11) | −0.0090 (12) | 0.0058 (12) |
| C17 | 0.0225 (14) | 0.0299 (16) | 0.0145 (14) | −0.0085 (11) | 0.0008 (10) | 0.0059 (12) |
| Br1—C12 | 1.873 (2) | C5—C6 | 1.387 (3) |
| Cl1—C14 | 1.713 (3) | C5—H5 | 0.9300 |
| O1—C4 | 1.375 (3) | C6—H6 | 0.9300 |
| O1—C7 | 1.430 (3) | C7—C8 | 1.510 (3) |
| O2—C9 | 1.222 (3) | C7—H7A | 0.9700 |
| N1—C9 | 1.350 (3) | C7—H7B | 0.9700 |
| N1—C1 | 1.419 (3) | C8—H8A | 0.9600 |
| N1—H1 | 0.877 (9) | C8—H8B | 0.9600 |
| N2—C12 | 1.322 (3) | C8—H8C | 0.9600 |
| N2—N3 | 1.367 (2) | C9—C10 | 1.488 (3) |
| N3—C10 | 1.376 (3) | C10—C11 | 1.367 (3) |
| N3—C13 | 1.429 (3) | C11—C12 | 1.391 (3) |
| N4—C17 | 1.330 (3) | C11—H11 | 0.9300 |
| N4—C13 | 1.333 (3) | C13—C14 | 1.384 (3) |
| C1—C6 | 1.379 (3) | C14—C15 | 1.386 (4) |
| C1—C2 | 1.389 (3) | C15—C16 | 1.373 (4) |
| C2—C3 | 1.378 (3) | C15—H15 | 0.9300 |
| C2—H2 | 0.9300 | C16—C17 | 1.381 (4) |
| C3—C4 | 1.379 (3) | C16—H16 | 0.9300 |
| C3—H3 | 0.9300 | C17—H17 | 0.9300 |
| C4—C5 | 1.384 (3) | ||
| C4—O1—C7 | 116.83 (18) | C7—C8—H8A | 109.5 |
| C9—N1—C1 | 126.63 (19) | C7—C8—H8B | 109.5 |
| C9—N1—H1 | 117.9 (14) | H8A—C8—H8B | 109.5 |
| C1—N1—H1 | 115.4 (14) | C7—C8—H8C | 109.5 |
| C12—N2—N3 | 103.58 (17) | H8A—C8—H8C | 109.5 |
| N2—N3—C10 | 111.61 (18) | H8B—C8—H8C | 109.5 |
| N2—N3—C13 | 116.61 (17) | O2—C9—N1 | 125.03 (19) |
| C10—N3—C13 | 130.86 (17) | O2—C9—C10 | 120.47 (19) |
| C17—N4—C13 | 117.5 (2) | N1—C9—C10 | 114.5 (2) |
| C6—C1—C2 | 118.5 (2) | C11—C10—N3 | 106.54 (18) |
| C6—C1—N1 | 118.0 (2) | C11—C10—C9 | 133.6 (2) |
| C2—C1—N1 | 123.5 (2) | N3—C10—C9 | 119.8 (2) |
| C3—C2—C1 | 119.7 (2) | C10—C11—C12 | 104.7 (2) |
| C3—C2—H2 | 120.2 | C10—C11—H11 | 127.6 |
| C1—C2—H2 | 120.2 | C12—C11—H11 | 127.6 |
| C2—C3—C4 | 121.7 (2) | N2—C12—C11 | 113.5 (2) |
| C2—C3—H3 | 119.2 | N2—C12—Br1 | 120.16 (16) |
| C4—C3—H3 | 119.2 | C11—C12—Br1 | 126.31 (18) |
| O1—C4—C3 | 115.6 (2) | N4—C13—C14 | 123.2 (2) |
| O1—C4—C5 | 125.3 (2) | N4—C13—N3 | 114.5 (2) |
| C3—C4—C5 | 119.1 (2) | C14—C13—N3 | 122.1 (2) |
| C4—C5—C6 | 119.0 (2) | C13—C14—C15 | 118.3 (2) |
| C4—C5—H5 | 120.5 | C13—C14—Cl1 | 120.6 (2) |
| C6—C5—H5 | 120.5 | C15—C14—Cl1 | 121.1 (2) |
| C1—C6—C5 | 122.0 (2) | C16—C15—C14 | 119.0 (2) |
| C1—C6—H6 | 119.0 | C16—C15—H15 | 120.5 |
| C5—C6—H6 | 119.0 | C14—C15—H15 | 120.5 |
| O1—C7—C8 | 107.1 (2) | C15—C16—C17 | 118.5 (2) |
| O1—C7—H7A | 110.3 | C15—C16—H16 | 120.7 |
| C8—C7—H7A | 110.3 | C17—C16—H16 | 120.7 |
| O1—C7—H7B | 110.3 | N4—C17—C16 | 123.5 (3) |
| C8—C7—H7B | 110.3 | N4—C17—H17 | 118.2 |
| H7A—C7—H7B | 108.6 | C16—C17—H17 | 118.2 |
| C12—N2—N3—C10 | 1.4 (3) | N1—C9—C10—C11 | 5.7 (4) |
| C12—N2—N3—C13 | 171.6 (2) | O2—C9—C10—N3 | 6.4 (4) |
| C9—N1—C1—C6 | −167.1 (2) | N1—C9—C10—N3 | −172.7 (2) |
| C9—N1—C1—C2 | 13.5 (4) | N3—C10—C11—C12 | 1.4 (3) |
| C6—C1—C2—C3 | −1.0 (4) | C9—C10—C11—C12 | −177.1 (3) |
| N1—C1—C2—C3 | 178.3 (3) | N3—N2—C12—C11 | −0.4 (3) |
| C1—C2—C3—C4 | 0.2 (5) | N3—N2—C12—Br1 | −179.10 (15) |
| C7—O1—C4—C3 | −174.8 (2) | C10—C11—C12—N2 | −0.6 (3) |
| C7—O1—C4—C5 | 5.3 (4) | C10—C11—C12—Br1 | 177.93 (18) |
| C2—C3—C4—O1 | −179.5 (3) | C17—N4—C13—C14 | 1.5 (3) |
| C2—C3—C4—C5 | 0.4 (5) | C17—N4—C13—N3 | 177.11 (17) |
| O1—C4—C5—C6 | 179.7 (2) | N2—N3—C13—N4 | −69.3 (2) |
| C3—C4—C5—C6 | −0.1 (4) | C10—N3—C13—N4 | 98.6 (3) |
| C2—C1—C6—C5 | 1.4 (4) | N2—N3—C13—C14 | 106.3 (2) |
| N1—C1—C6—C5 | −178.0 (2) | C10—N3—C13—C14 | −85.8 (3) |
| C4—C5—C6—C1 | −0.8 (4) | N4—C13—C14—C15 | −1.8 (3) |
| C4—O1—C7—C8 | −179.8 (2) | N3—C13—C14—C15 | −177.04 (19) |
| C1—N1—C9—O2 | 0.4 (4) | N4—C13—C14—Cl1 | 176.20 (16) |
| C1—N1—C9—C10 | 179.5 (2) | N3—C13—C14—Cl1 | 0.9 (3) |
| N2—N3—C10—C11 | −1.8 (3) | C13—C14—C15—C16 | 0.7 (3) |
| C13—N3—C10—C11 | −170.2 (2) | Cl1—C14—C15—C16 | −177.25 (17) |
| N2—N3—C10—C9 | 176.95 (19) | C14—C15—C16—C17 | 0.5 (3) |
| C13—N3—C10—C9 | 8.6 (4) | C13—N4—C17—C16 | −0.2 (3) |
| O2—C9—C10—C11 | −175.3 (3) | C15—C16—C17—N4 | −0.7 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···N4i | 0.88 (1) | 2.21 (1) | 3.059 (3) | 165 (2) |
| C2—H2···O2 | 0.93 | 2.26 | 2.850 (3) | 121 |
| C6—H6···N4i | 0.93 | 2.60 | 3.358 (3) | 140 |
| C8—H8A···O2ii | 0.96 | 2.45 | 3.397 (3) | 168 |
| C11—H11···N4i | 0.93 | 2.55 | 3.390 (3) | 151 |
| C16—H16···O2iii | 0.93 | 2.33 | 3.244 (3) | 167 |
| Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) x, −y+3/2, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···N4i | 0.88 (1) | 2.21 (1) | 3.059 (3) | 165 (2) |
| C2—H2···O2 | 0.93 | 2.26 | 2.850 (3) | 121 |
| C6—H6···N4i | 0.93 | 2.60 | 3.358 (3) | 140 |
| C8—H8A···O2ii | 0.96 | 2.45 | 3.397 (3) | 168 |
| C11—H11···N4i | 0.93 | 2.55 | 3.390 (3) | 151 |
| C16—H16···O2iii | 0.93 | 2.33 | 3.244 (3) | 167 |
| Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) x, −y+3/2, z−1/2. |
This work was supported by the National Natural Science Foundation of China (No. 20872069).
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Due to the capability of insects to rapidly develop resistance, the discovery of agents that act on new biochemical targets is an important tool for effective pest management. Calcium channels, in particular, the ryanodine receptors (RyR) represent an attractive biological target for insect control and thus offer excellent promise in integrated pest management strategies.
Many pesticide contain amide structures (Liu et al. 2007; Dong et al. 2008a,b; Liu et al. 2009a,b,c). Recently, diamides have attracted considerable attention in the field of agrochemistry, owing to their prominent insecticidal activity (Gewehr et al. 2007), unique modes of action and good environmental profiles.
Thus, a series of novel amides containing N-pyridylpyrazole were synthesized and their insecticidal activities were tested. Here we present the crystal structure of the title compound,(I), which has been determined during a search for relationships between the structure and insecticidal activity of the above derivatives.
The molecular structure of title compound (Fig.1) reveals that the pyrazole ring is coplanar with the benzene ring [dihedral angle 179.5 (2)°] whereas the pyrazole ring is almost perpendicular to 3-chlorpyridine ring [dihedral angle 106.3 (2)°]. In the crystal packing dominating N—H···N interaction and weak C—H···O and C—H···N contacts were observed (Table 1, Fig. 2).