Abstract
In the title compound, C25H13Cl2F4N3, there are four planar systems, viz. three benzene rings and a pyrazolo[1,5-a]pyrimidine system [r.m.s. deviation = 0.002 Å]. The dihedral angle between the dichlorophenyl ring and the unsubstituted phenyl ring is 69.95 (5)°, while that between the fluorophenyl ring and the unsubstituted phenyl ring is 7.97 (10)°. The crystal packing is dominated by van der Waals interactions. A Cl⋯Cl interaction of 3.475 (3) Å also occurs.
Related literature
For background information and the related structures, see: Liu et al. (2012 ▶); Frizzo et al. (2008 ▶); Bui et al. (2009 ▶). For the synthesis of other pyrozolo[1,5-a]pyrimidine derivatives and for their pharmacological applications, see: Fraley et al. (2012 ▶); Dalinger et al. (2005 ▶); Dennis et al. (2004 ▶).
Experimental
Crystal data
C25H13Cl2F4N3
M r = 502.28
Monoclinic,
a = 9.0826 (18) Å
b = 9.0606 (18) Å
c = 27.259 (6) Å
β = 99.46 (3)°
V = 2212.7 (8) Å3
Z = 4
Mo Kα radiation
μ = 0.35 mm−1
T = 293 K
0.24 × 0.22 × 0.20 mm
Data collection
Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.922, T max = 0.934
15847 measured reflections
3895 independent reflections
3056 reflections with I > 2σ(I)
R int = 0.041
Refinement
R[F 2 > 2σ(F 2)] = 0.051
wR(F 2) = 0.143
S = 1.09
3895 reflections
308 parameters
H-atom parameters constrained
Δρmax = 0.37 e Å−3
Δρmin = −0.46 e Å−3
Data collection: RAPID-AUTO (Rigaku, 1998) ▶; cell refinement: RAPID-AUTO ▶; data reduction: CrystalClear (Rigaku/MSC, 2005 ▶); 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.
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023641/kp2419sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023641/kp2419Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812023641/kp2419Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the State Key Laboratory of Elemento-organic Chemistry, Nankai University, for the X-ray data collection.
supplementary crystallographic information
Comment
The pyrazolo[1,5-a]pyrimidine structural motif may be found in a large number of pharmaceutical agents with a diverse range of physiological activities, for example, antiepileptic agents, anxiolytics, antidepressants, agents for treatment of sleep disorders and oncolytics. A series of antagonist of protease-activated PAR2 receptors were reported (Fraley,et al., 2012 and Dalinger,et al., 2005). As a part of our ongoing study of pyrazolo[1,5-a]pyrimidine derivatives containing 5-(4-fluorophenyl) and 3-(2,4-dichlorophenyl) substituents (Liu,et al., 2012), we report herein the crystal structure of the title compound.
The title molecule (Fig. 1) bond lengths and angles are generally within normal ranges. The dihedral angles between fluorobenzene ring and benzene ring is 7.97°. The dihedral angle between dichlorophenyl ring and benzene ring is 69.95°. The torsion angles C(16)—C(17)—C(18)—C(19), N(2)—N(1)—C(1)—C(2), C(21)—C(22)—C(23)—F(4) and C(10)—C(11)—C(12)—Cl(2) are -178.71 (19), 175.35 (17), -178.4 (2) and -179.9 (2), respectively. The crystal structure is held together by van der Waals forces and pronounced Cl···Cl interaction of 3.475 (3) Å (Bui, et al., 2009).
Experimental
A mixture of the corresponding 4-(2,4-dichlorophenyl)-3-phenyl-1H-pyrazol-5-amine (1.50 g, 4.93 mmol) and the 4,4,4-trifluoro-1-(4-fluorophenyl)butane-1,3-dione (1.27 g, 5.42 6 mmol) in a flask (25 mL) was heated at 453–458 K for 2.5 h, allowing elimination of the water evolved. After cooling to room temperature, the solid in the flask was recrystallised from methanol to yield the title compound as a yellow solid (1.55 g, 62.58%). Crystals suitable for X-ray analysis were obtained from EtOH : EtOAc(1:1) solution mixture by slow evaporation.
Refinement
All H atoms were geometrically positioned (C—H 0.93 Å) and treated as riding, with Uiso(H) = 1.2Ueq(C).Due to lack of heavy atoms, Friedel pairs were merged in refinement.
Figures
Fig. 1.
The structure of C25H13Cl2F4N3 with all non-H atom-labelling scheme and ellipsoids drawn at the 50% probability level.
Crystal data
| C25H13Cl2F4N3 | F(000) = 1016 |
| Mr = 502.28 | Dx = 1.508 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 5009 reflections |
| a = 9.0826 (18) Å | θ = 2.3–27.9° |
| b = 9.0606 (18) Å | µ = 0.35 mm−1 |
| c = 27.259 (6) Å | T = 293 K |
| β = 99.46 (3)° | Prism, yellow |
| V = 2212.7 (8) Å3 | 0.24 × 0.22 × 0.20 mm |
| Z = 4 |
Data collection
| Rigaku Saturn diffractometer | 3895 independent reflections |
| Radiation source: rotating anode | 3056 reflections with I > 2σ(I) |
| Confocal monochromator | Rint = 0.041 |
| ω scans | θmax = 25.0°, θmin = 2.4° |
| Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | h = −10→10 |
| Tmin = 0.922, Tmax = 0.934 | k = −10→7 |
| 15847 measured reflections | l = −30→32 |
Refinement
| 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)] = 0.051 | H-atom parameters constrained |
| wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0833P)2 + 0.040P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max = 0.001 |
| 3895 reflections | Δρmax = 0.37 e Å−3 |
| 308 parameters | Δρmin = −0.46 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.028 (3) |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 1.31929 (9) | 0.44828 (10) | 0.47969 (3) | 0.0868 (3) | |
| Cl2 | 0.94948 (12) | 0.20741 (11) | 0.59085 (3) | 0.1024 (4) | |
| F1 | 1.09069 (17) | 0.35785 (15) | 0.20644 (5) | 0.0619 (4) | |
| F2 | 1.2102 (2) | 0.5478 (2) | 0.23496 (6) | 0.0886 (6) | |
| F3 | 0.9955 (2) | 0.56762 (17) | 0.18909 (5) | 0.0831 (6) | |
| F4 | 0.24299 (18) | 0.7892 (2) | 0.32444 (6) | 0.0917 (6) | |
| N1 | 1.2012 (2) | 0.33960 (19) | 0.31669 (6) | 0.0413 (4) | |
| N2 | 1.0698 (2) | 0.41358 (18) | 0.31156 (6) | 0.0385 (4) | |
| N3 | 0.8699 (2) | 0.47095 (19) | 0.35650 (6) | 0.0401 (4) | |
| C1 | 1.2191 (2) | 0.2873 (2) | 0.36384 (7) | 0.0388 (5) | |
| C2 | 1.3488 (2) | 0.1903 (2) | 0.37979 (8) | 0.0432 (5) | |
| C3 | 1.4710 (3) | 0.1954 (3) | 0.35534 (9) | 0.0542 (6) | |
| H3 | 1.4737 | 0.2649 | 0.3304 | 0.065* | |
| C4 | 1.5895 (3) | 0.0981 (3) | 0.36768 (10) | 0.0670 (8) | |
| H4 | 1.6707 | 0.1023 | 0.3509 | 0.080* | |
| C5 | 1.5865 (3) | −0.0044 (3) | 0.40471 (11) | 0.0727 (9) | |
| H5 | 1.6655 | −0.0701 | 0.4129 | 0.087* | |
| C6 | 1.4674 (4) | −0.0098 (3) | 0.42954 (11) | 0.0731 (8) | |
| H6 | 1.4664 | −0.0782 | 0.4549 | 0.088* | |
| C7 | 1.3487 (3) | 0.0857 (3) | 0.41720 (9) | 0.0594 (7) | |
| H7 | 1.2678 | 0.0802 | 0.4341 | 0.071* | |
| C8 | 1.1017 (2) | 0.3286 (2) | 0.38894 (7) | 0.0395 (5) | |
| C9 | 1.0711 (2) | 0.2977 (2) | 0.43952 (7) | 0.0402 (5) | |
| C10 | 1.1586 (3) | 0.3478 (2) | 0.48288 (8) | 0.0468 (6) | |
| C11 | 1.1222 (3) | 0.3204 (3) | 0.52918 (8) | 0.0553 (7) | |
| H11 | 1.1831 | 0.3551 | 0.5576 | 0.066* | |
| C12 | 0.9960 (3) | 0.2419 (3) | 0.53295 (8) | 0.0592 (7) | |
| C13 | 0.9050 (3) | 0.1923 (3) | 0.49108 (10) | 0.0747 (9) | |
| H13 | 0.8181 | 0.1407 | 0.4936 | 0.090* | |
| C14 | 0.9437 (3) | 0.2199 (3) | 0.44528 (9) | 0.0620 (7) | |
| H14 | 0.8820 | 0.1849 | 0.4170 | 0.074* | |
| C15 | 1.0032 (2) | 0.4081 (2) | 0.35423 (7) | 0.0378 (5) | |
| C16 | 0.8006 (2) | 0.5390 (2) | 0.31605 (7) | 0.0386 (5) | |
| C17 | 0.8643 (3) | 0.5463 (2) | 0.27171 (8) | 0.0424 (5) | |
| H17 | 0.8129 | 0.5937 | 0.2438 | 0.051* | |
| C18 | 0.9989 (2) | 0.4847 (2) | 0.27000 (7) | 0.0394 (5) | |
| C19 | 1.0751 (3) | 0.4900 (3) | 0.22528 (8) | 0.0461 (6) | |
| C20 | 0.6539 (2) | 0.6071 (2) | 0.31877 (7) | 0.0396 (5) | |
| C21 | 0.5912 (3) | 0.7106 (3) | 0.28349 (9) | 0.0493 (6) | |
| H21 | 0.6427 | 0.7381 | 0.2581 | 0.059* | |
| C22 | 0.4542 (3) | 0.7726 (3) | 0.28576 (9) | 0.0573 (7) | |
| H22 | 0.4130 | 0.8419 | 0.2623 | 0.069* | |
| C23 | 0.3796 (3) | 0.7307 (3) | 0.32307 (10) | 0.0576 (7) | |
| C24 | 0.4372 (3) | 0.6316 (3) | 0.35902 (9) | 0.0564 (6) | |
| H24 | 0.3848 | 0.6061 | 0.3844 | 0.068* | |
| C25 | 0.5753 (3) | 0.5702 (2) | 0.35670 (8) | 0.0473 (6) | |
| H25 | 0.6163 | 0.5030 | 0.3809 | 0.057* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0765 (6) | 0.1313 (7) | 0.0511 (4) | −0.0570 (5) | 0.0062 (4) | −0.0089 (4) |
| Cl2 | 0.1446 (9) | 0.1281 (8) | 0.0411 (4) | −0.0592 (6) | 0.0350 (5) | −0.0028 (4) |
| F1 | 0.0830 (11) | 0.0617 (9) | 0.0432 (8) | 0.0200 (7) | 0.0171 (7) | −0.0052 (6) |
| F2 | 0.0899 (13) | 0.1194 (15) | 0.0648 (10) | −0.0465 (11) | 0.0371 (9) | −0.0103 (9) |
| F3 | 0.1145 (14) | 0.0927 (12) | 0.0507 (9) | 0.0534 (10) | 0.0388 (9) | 0.0330 (8) |
| F4 | 0.0567 (10) | 0.1403 (16) | 0.0836 (12) | 0.0343 (10) | 0.0276 (9) | 0.0172 (11) |
| N1 | 0.0423 (11) | 0.0467 (10) | 0.0346 (9) | −0.0032 (8) | 0.0056 (8) | −0.0020 (8) |
| N2 | 0.0449 (11) | 0.0409 (10) | 0.0303 (9) | 0.0002 (8) | 0.0075 (8) | 0.0001 (7) |
| N3 | 0.0425 (10) | 0.0471 (10) | 0.0315 (9) | −0.0027 (8) | 0.0083 (8) | −0.0011 (8) |
| C1 | 0.0382 (12) | 0.0458 (12) | 0.0321 (11) | −0.0077 (9) | 0.0049 (9) | −0.0040 (9) |
| C2 | 0.0425 (13) | 0.0500 (13) | 0.0356 (11) | −0.0023 (10) | 0.0021 (10) | −0.0076 (10) |
| C3 | 0.0491 (14) | 0.0662 (15) | 0.0459 (14) | −0.0023 (12) | 0.0033 (11) | −0.0048 (12) |
| C4 | 0.0484 (16) | 0.087 (2) | 0.0648 (17) | 0.0074 (14) | 0.0059 (13) | −0.0123 (16) |
| C5 | 0.0590 (19) | 0.0739 (18) | 0.080 (2) | 0.0197 (15) | −0.0047 (16) | −0.0118 (16) |
| C6 | 0.080 (2) | 0.0664 (17) | 0.0702 (19) | 0.0159 (16) | 0.0042 (16) | 0.0117 (15) |
| C7 | 0.0614 (16) | 0.0612 (15) | 0.0560 (16) | 0.0081 (13) | 0.0108 (13) | 0.0055 (12) |
| C8 | 0.0430 (12) | 0.0447 (12) | 0.0299 (10) | −0.0063 (9) | 0.0036 (9) | −0.0008 (9) |
| C9 | 0.0408 (12) | 0.0465 (12) | 0.0320 (11) | −0.0018 (10) | 0.0028 (9) | 0.0022 (9) |
| C10 | 0.0486 (14) | 0.0560 (14) | 0.0344 (12) | −0.0109 (11) | 0.0024 (10) | −0.0003 (10) |
| C11 | 0.0632 (16) | 0.0666 (16) | 0.0337 (12) | −0.0140 (13) | 0.0010 (11) | −0.0032 (11) |
| C12 | 0.0747 (18) | 0.0703 (16) | 0.0346 (13) | −0.0133 (14) | 0.0148 (12) | 0.0029 (11) |
| C13 | 0.0732 (19) | 0.104 (2) | 0.0478 (15) | −0.0433 (17) | 0.0131 (14) | 0.0027 (15) |
| C14 | 0.0591 (16) | 0.0897 (19) | 0.0355 (13) | −0.0285 (14) | 0.0028 (11) | −0.0048 (12) |
| C15 | 0.0424 (12) | 0.0442 (12) | 0.0274 (10) | −0.0045 (9) | 0.0071 (9) | −0.0028 (9) |
| C16 | 0.0439 (12) | 0.0378 (11) | 0.0338 (11) | −0.0055 (9) | 0.0052 (9) | −0.0028 (9) |
| C17 | 0.0494 (14) | 0.0440 (12) | 0.0341 (11) | 0.0012 (10) | 0.0074 (10) | 0.0014 (9) |
| C18 | 0.0518 (14) | 0.0371 (11) | 0.0303 (11) | −0.0035 (10) | 0.0095 (10) | −0.0006 (9) |
| C19 | 0.0576 (15) | 0.0468 (13) | 0.0358 (12) | 0.0053 (11) | 0.0133 (11) | 0.0039 (10) |
| C20 | 0.0407 (12) | 0.0421 (12) | 0.0362 (11) | −0.0068 (9) | 0.0064 (9) | −0.0043 (9) |
| C21 | 0.0441 (13) | 0.0639 (15) | 0.0404 (12) | −0.0012 (11) | 0.0080 (10) | 0.0047 (11) |
| C22 | 0.0495 (14) | 0.0713 (16) | 0.0504 (14) | 0.0128 (12) | 0.0064 (12) | 0.0111 (12) |
| C23 | 0.0412 (14) | 0.0759 (17) | 0.0563 (15) | 0.0061 (12) | 0.0093 (12) | −0.0060 (13) |
| C24 | 0.0552 (15) | 0.0684 (16) | 0.0504 (14) | −0.0040 (13) | 0.0227 (12) | −0.0013 (13) |
| C25 | 0.0540 (14) | 0.0510 (13) | 0.0389 (12) | −0.0036 (11) | 0.0134 (11) | 0.0012 (10) |
Geometric parameters (Å, º)
| Cl1—C10 | 1.734 (2) | C8—C9 | 1.477 (3) |
| Cl2—C12 | 1.728 (2) | C9—C14 | 1.386 (3) |
| F1—C19 | 1.320 (3) | C9—C10 | 1.387 (3) |
| F2—C19 | 1.320 (3) | C10—C11 | 1.379 (3) |
| F3—C19 | 1.325 (2) | C11—C12 | 1.367 (3) |
| F4—C23 | 1.356 (3) | C11—H11 | 0.9300 |
| N1—C1 | 1.354 (3) | C12—C13 | 1.370 (3) |
| N1—N2 | 1.356 (2) | C13—C14 | 1.375 (3) |
| N2—C18 | 1.369 (3) | C13—H13 | 0.9300 |
| N2—C15 | 1.397 (3) | C14—H14 | 0.9300 |
| N3—C16 | 1.328 (3) | C16—C17 | 1.425 (3) |
| N3—C15 | 1.349 (3) | C16—C20 | 1.481 (3) |
| C1—C8 | 1.409 (3) | C17—C18 | 1.352 (3) |
| C1—C2 | 1.477 (3) | C17—H17 | 0.9300 |
| C2—C3 | 1.386 (3) | C18—C19 | 1.498 (3) |
| C2—C7 | 1.392 (3) | C20—C25 | 1.390 (3) |
| C3—C4 | 1.389 (4) | C20—C21 | 1.396 (3) |
| C3—H3 | 0.9300 | C21—C22 | 1.376 (3) |
| C4—C5 | 1.375 (4) | C21—H21 | 0.9300 |
| C4—H4 | 0.9300 | C22—C23 | 1.365 (4) |
| C5—C6 | 1.369 (4) | C22—H22 | 0.9300 |
| C5—H5 | 0.9300 | C23—C24 | 1.368 (4) |
| C6—C7 | 1.380 (4) | C24—C25 | 1.384 (3) |
| C6—H6 | 0.9300 | C24—H24 | 0.9300 |
| C7—H7 | 0.9300 | C25—H25 | 0.9300 |
| C8—C15 | 1.391 (3) | ||
| C1—N1—N2 | 103.71 (17) | C12—C13—H13 | 120.4 |
| N1—N2—C18 | 127.17 (18) | C14—C13—H13 | 120.4 |
| N1—N2—C15 | 112.99 (16) | C13—C14—C9 | 122.6 (2) |
| C18—N2—C15 | 119.81 (18) | C13—C14—H14 | 118.7 |
| C16—N3—C15 | 117.66 (18) | C9—C14—H14 | 118.7 |
| N1—C1—C8 | 112.68 (18) | N3—C15—C8 | 131.98 (19) |
| N1—C1—C2 | 116.95 (19) | N3—C15—N2 | 122.52 (18) |
| C8—C1—C2 | 130.22 (19) | C8—C15—N2 | 105.50 (19) |
| C3—C2—C7 | 118.2 (2) | N3—C16—C17 | 121.5 (2) |
| C3—C2—C1 | 120.1 (2) | N3—C16—C20 | 117.33 (19) |
| C7—C2—C1 | 121.6 (2) | C17—C16—C20 | 121.14 (19) |
| C2—C3—C4 | 120.8 (2) | C18—C17—C16 | 120.4 (2) |
| C2—C3—H3 | 119.6 | C18—C17—H17 | 119.8 |
| C4—C3—H3 | 119.6 | C16—C17—H17 | 119.8 |
| C5—C4—C3 | 119.9 (3) | C17—C18—N2 | 118.08 (19) |
| C5—C4—H4 | 120.0 | C17—C18—C19 | 123.80 (19) |
| C3—C4—H4 | 120.0 | N2—C18—C19 | 118.1 (2) |
| C6—C5—C4 | 119.9 (3) | F1—C19—F2 | 106.4 (2) |
| C6—C5—H5 | 120.0 | F1—C19—F3 | 105.79 (17) |
| C4—C5—H5 | 120.0 | F2—C19—F3 | 108.3 (2) |
| C5—C6—C7 | 120.4 (3) | F1—C19—C18 | 112.40 (18) |
| C5—C6—H6 | 119.8 | F2—C19—C18 | 112.87 (18) |
| C7—C6—H6 | 119.8 | F3—C19—C18 | 110.76 (19) |
| C6—C7—C2 | 120.7 (3) | C25—C20—C21 | 118.2 (2) |
| C6—C7—H7 | 119.6 | C25—C20—C16 | 120.87 (19) |
| C2—C7—H7 | 119.6 | C21—C20—C16 | 120.9 (2) |
| C15—C8—C1 | 105.08 (18) | C22—C21—C20 | 120.9 (2) |
| C15—C8—C9 | 122.3 (2) | C22—C21—H21 | 119.6 |
| C1—C8—C9 | 132.56 (19) | C20—C21—H21 | 119.6 |
| C14—C9—C10 | 116.2 (2) | C23—C22—C21 | 118.9 (2) |
| C14—C9—C8 | 119.36 (18) | C23—C22—H22 | 120.6 |
| C10—C9—C8 | 124.3 (2) | C21—C22—H22 | 120.6 |
| C11—C10—C9 | 122.1 (2) | F4—C23—C22 | 118.7 (2) |
| C11—C10—Cl1 | 118.08 (17) | F4—C23—C24 | 118.7 (2) |
| C9—C10—Cl1 | 119.85 (17) | C22—C23—C24 | 122.6 (2) |
| C12—C11—C10 | 119.5 (2) | C23—C24—C25 | 118.3 (2) |
| C12—C11—H11 | 120.2 | C23—C24—H24 | 120.9 |
| C10—C11—H11 | 120.2 | C25—C24—H24 | 120.9 |
| C11—C12—C13 | 120.4 (2) | C24—C25—C20 | 121.2 (2) |
| C11—C12—Cl2 | 119.78 (19) | C24—C25—H25 | 119.4 |
| C13—C12—Cl2 | 119.8 (2) | C20—C25—H25 | 119.4 |
| C12—C13—C14 | 119.2 (2) | ||
| C1—N1—N2—C18 | −178.37 (19) | C1—C8—C15—N3 | 177.8 (2) |
| C1—N1—N2—C15 | −0.6 (2) | C9—C8—C15—N3 | −0.1 (3) |
| N2—N1—C1—C8 | −0.7 (2) | C1—C8—C15—N2 | −2.0 (2) |
| N2—N1—C1—C2 | 175.35 (17) | C9—C8—C15—N2 | −179.81 (18) |
| N1—C1—C2—C3 | 22.1 (3) | N1—N2—C15—N3 | −178.07 (17) |
| C8—C1—C2—C3 | −162.6 (2) | C18—N2—C15—N3 | −0.1 (3) |
| N1—C1—C2—C7 | −153.9 (2) | N1—N2—C15—C8 | 1.7 (2) |
| C8—C1—C2—C7 | 21.4 (3) | C18—N2—C15—C8 | 179.63 (17) |
| C7—C2—C3—C4 | 0.4 (3) | C15—N3—C16—C17 | −0.2 (3) |
| C1—C2—C3—C4 | −175.6 (2) | C15—N3—C16—C20 | 179.71 (17) |
| C2—C3—C4—C5 | −0.3 (4) | N3—C16—C17—C18 | −0.7 (3) |
| C3—C4—C5—C6 | −0.4 (4) | C20—C16—C17—C18 | 179.40 (18) |
| C4—C5—C6—C7 | 1.0 (4) | C16—C17—C18—N2 | 1.2 (3) |
| C5—C6—C7—C2 | −0.8 (4) | C16—C17—C18—C19 | −178.71 (19) |
| C3—C2—C7—C6 | 0.1 (4) | N1—N2—C18—C17 | 176.86 (18) |
| C1—C2—C7—C6 | 176.1 (2) | C15—N2—C18—C17 | −0.8 (3) |
| N1—C1—C8—C15 | 1.8 (2) | N1—N2—C18—C19 | −3.3 (3) |
| C2—C1—C8—C15 | −173.7 (2) | C15—N2—C18—C19 | 179.10 (19) |
| N1—C1—C8—C9 | 179.3 (2) | C17—C18—C19—F1 | −115.6 (2) |
| C2—C1—C8—C9 | 3.9 (4) | N2—C18—C19—F1 | 64.6 (3) |
| C15—C8—C9—C14 | 59.2 (3) | C17—C18—C19—F2 | 124.1 (2) |
| C1—C8—C9—C14 | −118.0 (3) | N2—C18—C19—F2 | −55.8 (3) |
| C15—C8—C9—C10 | −117.6 (2) | C17—C18—C19—F3 | 2.5 (3) |
| C1—C8—C9—C10 | 65.3 (3) | N2—C18—C19—F3 | −177.34 (19) |
| C14—C9—C10—C11 | 0.7 (4) | N3—C16—C20—C25 | −15.9 (3) |
| C8—C9—C10—C11 | 177.6 (2) | C17—C16—C20—C25 | 164.1 (2) |
| C14—C9—C10—Cl1 | −179.21 (19) | N3—C16—C20—C21 | 163.79 (19) |
| C8—C9—C10—Cl1 | −2.3 (3) | C17—C16—C20—C21 | −16.3 (3) |
| C9—C10—C11—C12 | −0.2 (4) | C25—C20—C21—C22 | −1.1 (3) |
| Cl1—C10—C11—C12 | 179.8 (2) | C16—C20—C21—C22 | 179.3 (2) |
| C10—C11—C12—C13 | −0.9 (4) | C20—C21—C22—C23 | −0.3 (4) |
| C10—C11—C12—Cl2 | −179.9 (2) | C21—C22—C23—F4 | −178.4 (2) |
| C11—C12—C13—C14 | 1.3 (5) | C21—C22—C23—C24 | 1.4 (4) |
| Cl2—C12—C13—C14 | −179.7 (2) | F4—C23—C24—C25 | 178.7 (2) |
| C12—C13—C14—C9 | −0.7 (5) | C22—C23—C24—C25 | −1.1 (4) |
| C10—C9—C14—C13 | −0.3 (4) | C23—C24—C25—C20 | −0.3 (4) |
| C8—C9—C14—C13 | −177.3 (3) | C21—C20—C25—C24 | 1.4 (3) |
| C16—N3—C15—C8 | −179.1 (2) | C16—C20—C25—C24 | −179.0 (2) |
| C16—N3—C15—N2 | 0.6 (3) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2419).
References
- Bui, T. T., Dahaoui, S., Lecomte, C., Desiraju, G. R. & Espinosa, E. (2009). Angew. Chem. Int. Ed. 48, 3838–3841. [DOI] [PubMed]
- Dalinger, I. L., Vatsadse, I. A., Shevelev, S. A. & Ivachtchenko, A. V. (2005). ACS Comb. Sci. 7, 236–245. [DOI] [PubMed]
- Dennis, R. C., Kathyn, E. C. & John, A. K. (2004). Bioorg. Med. Chem. Lett. 14, 5681–5684.
- Fraley, M. E., Rubino, R. S., Hoffman, W. F., Hambaugh, S. R., Arrington, K. L., Hungate, R. W., Bilodeau, M. T., Tebben, A. J., Rutledge, R. Z., Kendall, R. L., McFall, R. C., Huckle, W. R., Coll, K. E. & Thomas, K. A. (2012). Bioorg. Med. Chem. Lett. 12, 3537–3541. [DOI] [PubMed]
- Frizzo, C. P., Campos, P. T., Marzari, M. R. B., Machado, P. & Martins, M. A. P. (2008). Acta Cryst. E64, o212. [DOI] [PMC free article] [PubMed]
- Liu, J., Cai, Z.-Q., Wang, Y., Jiang, M.-J. & Xu, L.-F. (2012). Acta Cryst. E68, o1515. [DOI] [PMC free article] [PubMed]
- Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
- Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023641/kp2419sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023641/kp2419Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812023641/kp2419Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report