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organic compounds
The title compound, C18H16BrN3O, presents the expected molecular geometry. There are π–π interactions between neighbouring molecules, through the imine functionality, forming dimers in the crystal structure. Weak C—H
O interactions link the dimers, forming a chain structure.
O interactions link the dimers, forming a chain structure.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044540/bh2054sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044540/bh2054Isup2.hkl |
CCDC reference: 627317
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C)= 0.005 Å - R factor = 0.051
- wR factor = 0.113
- Data-to-parameter ratio = 15.4
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C)= 0.005 ÅcheckCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(E)-4-[(4-Bromobenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one top
Crystal data top
| C18H16BrN3O | F(000) = 1504 |
| Mr = 370.25 | Dx = 1.493 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 3812 reflections |
| a = 6.9803 (4) Å | θ = 2.1–25.4° |
| b = 17.5191 (9) Å | µ = 2.50 mm−1 |
| c = 26.9377 (14) Å | T = 291 K |
| V = 3294.2 (3) Å3 | Block, yellow |
| Z = 8 | 0.32 × 0.26 × 0.24 mm |
Data collection top
| Bruker SMART APEX CCD area-detector diffractometer | 3241 independent reflections |
| Radiation source: sealed tube | 2307 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.050 |
| φ and ω scans | θmax = 26.0°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −8→8 |
| Tmin = 0.460, Tmax = 0.550 | k = −21→21 |
| 19952 measured reflections | l = −33→33 |
Refinement top
| 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.113 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.05P)2 + 1.88P] where P = (Fo2 + 2Fc2)/3 |
| 3241 reflections | (Δ/σ)max < 0.001 |
| 210 parameters | Δρmax = 0.24 e Å−3 |
| 0 restraints | Δρmin = −0.28 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.5658 (6) | 0.7643 (2) | 0.65022 (14) | 0.0380 (9) | |
| C2 | 0.5504 (6) | 0.6850 (2) | 0.65020 (14) | 0.0435 (10) | |
| H2 | 0.4751 | 0.6607 | 0.6265 | 0.052* | |
| C3 | 0.6478 (6) | 0.6423 (2) | 0.68558 (15) | 0.0433 (9) | |
| H3 | 0.6376 | 0.5894 | 0.6856 | 0.052* | |
| C4 | 0.7604 (6) | 0.6787 (2) | 0.72102 (16) | 0.0467 (10) | |
| H4 | 0.8250 | 0.6501 | 0.7448 | 0.056* | |
| C5 | 0.7762 (6) | 0.7576 (2) | 0.72087 (15) | 0.0456 (9) | |
| H5 | 0.8520 | 0.7818 | 0.7445 | 0.055* | |
| C6 | 0.6793 (6) | 0.8007 (3) | 0.68551 (15) | 0.0458 (10) | |
| H6 | 0.6902 | 0.8536 | 0.6855 | 0.055* | |
| C7 | 0.5741 (6) | 0.8537 (2) | 0.57949 (14) | 0.0363 (8) | |
| C8 | 0.4456 (6) | 0.8586 (2) | 0.53658 (14) | 0.0424 (9) | |
| C9 | 0.2862 (5) | 0.8182 (2) | 0.54792 (13) | 0.0364 (8) | |
| C10 | 0.6380 (6) | 0.9253 (2) | 0.48153 (15) | 0.0437 (9) | |
| H10 | 0.7260 | 0.9315 | 0.5071 | 0.052* | |
| C11 | 0.6804 (5) | 0.9534 (2) | 0.43779 (14) | 0.0389 (8) | |
| C12 | 0.8582 (6) | 0.9871 (2) | 0.42999 (15) | 0.0419 (9) | |
| H12 | 0.9460 | 0.9904 | 0.4559 | 0.050* | |
| C13 | 0.9045 (5) | 1.0159 (2) | 0.38349 (14) | 0.0390 (9) | |
| H13 | 1.0231 | 1.0387 | 0.3783 | 0.047* | |
| C14 | 0.7742 (6) | 1.0107 (2) | 0.34478 (14) | 0.0428 (10) | |
| C15 | 0.5964 (6) | 0.9767 (2) | 0.35242 (15) | 0.0392 (9) | |
| H15 | 0.5091 | 0.9731 | 0.3264 | 0.047* | |
| C16 | 0.5497 (5) | 0.9481 (2) | 0.39907 (13) | 0.0370 (8) | |
| H16 | 0.4309 | 0.9254 | 0.4043 | 0.044* | |
| C17 | 0.1385 (6) | 0.7684 (2) | 0.62533 (14) | 0.0411 (9) | |
| H17A | 0.0848 | 0.8157 | 0.6367 | 0.062* | |
| H17B | 0.1826 | 0.7393 | 0.6533 | 0.062* | |
| H17C | 0.0424 | 0.7398 | 0.6078 | 0.062* | |
| C18 | 0.1081 (6) | 0.8101 (2) | 0.51640 (15) | 0.0451 (10) | |
| H18A | 0.0819 | 0.7570 | 0.5109 | 0.068* | |
| H18B | 0.1278 | 0.8350 | 0.4851 | 0.068* | |
| H18C | 0.0015 | 0.8332 | 0.5332 | 0.068* | |
| Br1 | 0.83900 (7) | 1.04881 (3) | 0.280562 (16) | 0.05384 (16) | |
| N1 | 0.4729 (5) | 0.81047 (18) | 0.61548 (11) | 0.0408 (8) | |
| N2 | 0.2996 (4) | 0.78398 (17) | 0.59204 (11) | 0.0362 (7) | |
| N3 | 0.4820 (5) | 0.88983 (18) | 0.49082 (11) | 0.0413 (8) | |
| O1 | 0.7378 (4) | 0.87729 (16) | 0.58694 (10) | 0.0445 (7) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.035 (2) | 0.038 (2) | 0.040 (2) | 0.0016 (16) | 0.0059 (17) | −0.0052 (16) |
| C2 | 0.042 (3) | 0.050 (2) | 0.038 (2) | 0.0017 (19) | −0.0068 (17) | −0.0125 (18) |
| C3 | 0.032 (2) | 0.045 (2) | 0.054 (2) | 0.0140 (19) | 0.0033 (18) | −0.0006 (17) |
| C4 | 0.041 (2) | 0.042 (2) | 0.058 (2) | 0.0068 (19) | −0.010 (2) | 0.0040 (19) |
| C5 | 0.041 (2) | 0.049 (2) | 0.047 (2) | −0.0087 (18) | 0.0008 (19) | −0.0047 (19) |
| C6 | 0.034 (2) | 0.057 (3) | 0.047 (2) | −0.0109 (19) | −0.0026 (17) | −0.0036 (18) |
| C7 | 0.039 (2) | 0.0261 (18) | 0.043 (2) | −0.0021 (16) | 0.0008 (17) | 0.0004 (15) |
| C8 | 0.040 (2) | 0.047 (2) | 0.040 (2) | −0.0017 (18) | 0.0009 (17) | −0.0099 (18) |
| C9 | 0.035 (2) | 0.046 (2) | 0.0288 (18) | 0.0010 (17) | −0.0060 (15) | −0.0091 (15) |
| C10 | 0.044 (3) | 0.044 (2) | 0.043 (2) | 0.004 (2) | −0.0034 (19) | −0.0074 (17) |
| C11 | 0.030 (2) | 0.0382 (19) | 0.048 (2) | 0.0016 (18) | −0.0089 (16) | −0.0122 (18) |
| C12 | 0.030 (2) | 0.042 (2) | 0.054 (2) | −0.0048 (17) | −0.0065 (18) | −0.0093 (18) |
| C13 | 0.026 (2) | 0.040 (2) | 0.051 (2) | −0.0140 (16) | 0.0082 (16) | −0.0117 (17) |
| C14 | 0.049 (3) | 0.041 (2) | 0.0383 (19) | −0.0156 (18) | −0.0076 (17) | −0.0024 (16) |
| C15 | 0.031 (2) | 0.044 (2) | 0.042 (2) | −0.0122 (17) | −0.0126 (15) | 0.0105 (17) |
| C16 | 0.030 (2) | 0.037 (2) | 0.045 (2) | −0.0096 (16) | −0.0119 (16) | 0.0024 (16) |
| C17 | 0.039 (2) | 0.042 (2) | 0.0424 (19) | −0.0105 (18) | 0.0110 (18) | 0.0105 (16) |
| C18 | 0.045 (3) | 0.048 (2) | 0.043 (2) | −0.0088 (19) | −0.0126 (17) | −0.0018 (17) |
| Br1 | 0.0536 (3) | 0.0537 (3) | 0.0542 (3) | 0.0104 (2) | 0.0105 (2) | 0.0134 (2) |
| N1 | 0.041 (2) | 0.0386 (18) | 0.0427 (18) | −0.0135 (15) | −0.0047 (15) | −0.0019 (14) |
| N2 | 0.0347 (18) | 0.0332 (16) | 0.0407 (17) | −0.0127 (14) | 0.0013 (13) | −0.0086 (13) |
| N3 | 0.045 (2) | 0.0414 (19) | 0.0374 (17) | −0.0040 (16) | −0.0006 (15) | −0.0038 (13) |
| O1 | 0.0431 (16) | 0.0418 (15) | 0.0487 (16) | −0.0141 (13) | −0.0044 (13) | 0.0043 (12) |
Geometric parameters (Å, º) top
| C1—C6 | 1.392 (5) | C10—H10 | 0.9300 |
| C1—C2 | 1.393 (6) | C11—C16 | 1.389 (5) |
| C1—N1 | 1.396 (5) | C11—C12 | 1.391 (5) |
| C2—C3 | 1.390 (6) | C12—C13 | 1.388 (6) |
| C2—H2 | 0.9300 | C12—H12 | 0.9300 |
| C3—C4 | 1.391 (6) | C13—C14 | 1.387 (5) |
| C3—H3 | 0.9300 | C13—H13 | 0.9300 |
| C4—C5 | 1.387 (6) | C14—C15 | 1.392 (6) |
| C4—H4 | 0.9300 | C14—Br1 | 1.909 (4) |
| C5—C6 | 1.391 (6) | C15—C16 | 1.392 (5) |
| C5—H5 | 0.9300 | C15—H15 | 0.9300 |
| C6—H6 | 0.9300 | C16—H16 | 0.9300 |
| C7—O1 | 1.232 (5) | C17—N2 | 1.464 (5) |
| C7—N1 | 1.418 (5) | C17—H17A | 0.9600 |
| C7—C8 | 1.466 (5) | C17—H17B | 0.9600 |
| C8—C9 | 1.353 (6) | C17—H17C | 0.9600 |
| C8—N3 | 1.372 (5) | C18—H18A | 0.9600 |
| C9—N2 | 1.334 (5) | C18—H18B | 0.9600 |
| C9—C18 | 1.512 (5) | C18—H18C | 0.9600 |
| C10—N3 | 1.278 (5) | N1—N2 | 1.442 (4) |
| C10—C11 | 1.311 (6) | ||
| C6—C1—C2 | 120.1 (4) | C13—C12—H12 | 120.1 |
| C6—C1—N1 | 117.2 (3) | C11—C12—H12 | 120.1 |
| C2—C1—N1 | 122.8 (4) | C14—C13—C12 | 120.2 (4) |
| C3—C2—C1 | 120.0 (4) | C14—C13—H13 | 119.9 |
| C3—C2—H2 | 120.0 | C12—C13—H13 | 119.9 |
| C1—C2—H2 | 120.0 | C13—C14—C15 | 120.1 (4) |
| C2—C3—C4 | 120.0 (4) | C13—C14—Br1 | 120.2 (3) |
| C2—C3—H3 | 120.0 | C15—C14—Br1 | 119.7 (3) |
| C4—C3—H3 | 120.0 | C16—C15—C14 | 119.8 (3) |
| C5—C4—C3 | 120.0 (4) | C16—C15—H15 | 120.1 |
| C5—C4—H4 | 120.0 | C14—C15—H15 | 120.1 |
| C3—C4—H4 | 120.0 | C11—C16—C15 | 120.0 (3) |
| C4—C5—C6 | 120.3 (4) | C11—C16—H16 | 120.0 |
| C4—C5—H5 | 119.9 | C15—C16—H16 | 120.0 |
| C6—C5—H5 | 119.9 | N2—C17—H17A | 109.5 |
| C5—C6—C1 | 119.7 (4) | N2—C17—H17B | 109.5 |
| C5—C6—H6 | 120.1 | H17A—C17—H17B | 109.5 |
| C1—C6—H6 | 120.1 | N2—C17—H17C | 109.5 |
| O1—C7—N1 | 122.0 (3) | H17A—C17—H17C | 109.5 |
| O1—C7—C8 | 132.6 (4) | H17B—C17—H17C | 109.5 |
| N1—C7—C8 | 105.4 (3) | C9—C18—H18A | 109.5 |
| C9—C8—N3 | 124.3 (4) | C9—C18—H18B | 109.5 |
| C9—C8—C7 | 107.1 (3) | H18A—C18—H18B | 109.5 |
| N3—C8—C7 | 128.2 (4) | C9—C18—H18C | 109.5 |
| N2—C9—C8 | 112.2 (3) | H18A—C18—H18C | 109.5 |
| N2—C9—C18 | 121.0 (4) | H18B—C18—H18C | 109.5 |
| C8—C9—C18 | 126.7 (4) | C1—N1—C7 | 122.4 (3) |
| N3—C10—C11 | 123.4 (4) | C1—N1—N2 | 119.8 (3) |
| N3—C10—H10 | 118.3 | C7—N1—N2 | 106.9 (3) |
| C11—C10—H10 | 118.3 | C9—N2—N1 | 107.7 (3) |
| C10—C11—C16 | 120.1 (4) | C9—N2—C17 | 125.2 (3) |
| C10—C11—C12 | 119.8 (4) | N1—N2—C17 | 115.9 (3) |
| C16—C11—C12 | 120.1 (4) | C10—N3—C8 | 121.8 (4) |
| C13—C12—C11 | 119.9 (4) |
