organic compounds
The NH unit on the exocyclic C=C double bond in the title compound, C25H23N3O, interacts with the carbonyl group through an intramolecular hydrogen bond.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038438/bt2182sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038438/bt2182Isup2.hkl |
CCDC reference: 624007
Computing details top
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
4-[(Z)-(2,4-Dimethylphenylamino)phenylmethylene]-3-methyl-1-phenyl-1H- pyrazol-5(4H)-one top
Crystal data top
C25H23N3O | Z = 2 |
Mr = 381.46 | F(000) = 404 |
Triclinic, P1 | Dx = 1.223 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.909 (1) Å | Cell parameters from 1384 reflections |
b = 11.200 (1) Å | θ = 2.7–20.4° |
c = 13.239 (1) Å | µ = 0.08 mm−1 |
α = 106.410 (2)° | T = 295 K |
β = 106.327 (2)° | Block, yellow |
γ = 100.390 (2)° | 0.10 × 0.06 × 0.04 mm |
V = 1035.6 (2) Å3 |
Data collection top
Bruker SMART area-detector diffractometer | 2018 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.078 |
Graphite monochromator | θmax = 27.5°, θmin = 1.7° |
ω and φ scans | h = −10→10 |
10060 measured reflections | k = −14→14 |
4633 independent reflections | l = −17→17 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 0.83 | w = 1/[σ2(Fo2) + (0.047P)2] where P = (Fo2 + 2Fc2)/3 |
4633 reflections | (Δ/σ)max = 0.001 |
265 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 1.2316 (2) | 0.14575 (15) | 0.75272 (13) | 0.0714 (5) | |
N1 | 1.5387 (2) | 0.26624 (17) | 0.85053 (14) | 0.0569 (5) | |
N2 | 1.6439 (2) | 0.39594 (18) | 0.88910 (14) | 0.0613 (5) | |
N3 | 1.0293 (2) | 0.30363 (19) | 0.69866 (14) | 0.0610 (5) | |
H3N | 1.0457 | 0.2308 | 0.7020 | 0.073 | |
C1 | 1.6299 (3) | 0.1689 (2) | 0.85790 (17) | 0.0579 (6) | |
C2 | 1.5392 (3) | 0.0537 (2) | 0.8613 (2) | 0.0835 (8) | |
H2 | 1.4181 | 0.0391 | 0.8583 | 0.100* | |
C3 | 1.6288 (4) | −0.0393 (2) | 0.8690 (2) | 0.0960 (9) | |
H3 | 1.5672 | −0.1169 | 0.8714 | 0.115* | |
C4 | 1.8064 (4) | −0.0201 (3) | 0.8733 (2) | 0.0916 (9) | |
H4 | 1.8652 | −0.0842 | 0.8777 | 0.110* | |
C5 | 1.8966 (4) | 0.0942 (3) | 0.8709 (2) | 0.0907 (9) | |
H5 | 2.0178 | 0.1081 | 0.8742 | 0.109* | |
C6 | 1.8094 (3) | 0.1898 (3) | 0.8637 (2) | 0.0735 (7) | |
H6 | 1.8722 | 0.2679 | 0.8627 | 0.088* | |
C7 | 1.3562 (3) | 0.2510 (2) | 0.79753 (18) | 0.0560 (6) | |
C8 | 1.3434 (3) | 0.3791 (2) | 0.80392 (16) | 0.0514 (5) | |
C9 | 1.5279 (3) | 0.4613 (2) | 0.86177 (17) | 0.0560 (6) | |
C10 | 1.6025 (3) | 0.6043 (2) | 0.8930 (2) | 0.0764 (7) | |
H10A | 1.7338 | 0.6288 | 0.9276 | 0.115* | |
H10B | 1.5515 | 0.6492 | 0.9449 | 0.115* | |
H10C | 1.5703 | 0.6266 | 0.8266 | 0.115* | |
C11 | 1.1805 (3) | 0.4038 (2) | 0.75300 (17) | 0.0527 (6) | |
C12 | 1.1714 (3) | 0.5336 (2) | 0.75121 (18) | 0.0512 (5) | |
C13 | 1.1637 (3) | 0.5623 (2) | 0.65563 (19) | 0.0676 (7) | |
H13 | 1.1664 | 0.5003 | 0.5928 | 0.081* | |
C14 | 1.1518 (3) | 0.6829 (3) | 0.6531 (2) | 0.0807 (8) | |
H14 | 1.1476 | 0.7021 | 0.5886 | 0.097* | |
C15 | 1.1463 (3) | 0.7743 (3) | 0.7449 (3) | 0.0803 (8) | |
H15 | 1.1366 | 0.8550 | 0.7424 | 0.096* | |
C16 | 1.1551 (3) | 0.7474 (2) | 0.8403 (2) | 0.0776 (7) | |
H16 | 1.1518 | 0.8099 | 0.9028 | 0.093* | |
C17 | 1.1687 (3) | 0.6281 (2) | 0.84409 (19) | 0.0652 (6) | |
H17 | 1.1761 | 0.6106 | 0.9096 | 0.078* | |
C18 | 0.8445 (3) | 0.2952 (2) | 0.63569 (18) | 0.0539 (6) | |
C19 | 0.7652 (3) | 0.3951 (2) | 0.66224 (19) | 0.0686 (7) | |
H19 | 0.8316 | 0.4706 | 0.7238 | 0.082* | |
C20 | 0.5878 (3) | 0.3827 (2) | 0.5975 (2) | 0.0700 (7) | |
H20 | 0.5364 | 0.4506 | 0.6158 | 0.084* | |
C21 | 0.4858 (3) | 0.2715 (3) | 0.5065 (2) | 0.0643 (6) | |
C22 | 0.5661 (3) | 0.1726 (2) | 0.48343 (19) | 0.0666 (6) | |
H22 | 0.4977 | 0.0963 | 0.4232 | 0.080* | |
C23 | 0.7434 (3) | 0.1813 (2) | 0.54563 (19) | 0.0568 (6) | |
C24 | 0.2931 (3) | 0.2602 (3) | 0.4367 (2) | 0.1006 (9) | |
H24A | 0.2945 | 0.3295 | 0.4075 | 0.151* | |
H24B | 0.2180 | 0.2654 | 0.4827 | 0.151* | |
H24C | 0.2439 | 0.1784 | 0.3755 | 0.151* | |
C25 | 0.8245 (3) | 0.0713 (2) | 0.5134 (2) | 0.0881 (8) | |
H25A | 0.7379 | 0.0041 | 0.4461 | 0.132* | |
H25B | 0.8526 | 0.0374 | 0.5732 | 0.132* | |
H25C | 0.9350 | 0.1021 | 0.5004 | 0.132* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0513 (9) | 0.0629 (11) | 0.0876 (12) | 0.0201 (9) | 0.0088 (9) | 0.0217 (9) |
N1 | 0.0480 (11) | 0.0505 (12) | 0.0667 (12) | 0.0202 (9) | 0.0083 (9) | 0.0206 (10) |
N2 | 0.0531 (11) | 0.0623 (13) | 0.0635 (12) | 0.0181 (10) | 0.0104 (9) | 0.0239 (10) |
N3 | 0.0561 (12) | 0.0543 (13) | 0.0713 (13) | 0.0258 (10) | 0.0125 (10) | 0.0240 (10) |
C1 | 0.0535 (14) | 0.0608 (16) | 0.0562 (14) | 0.0274 (12) | 0.0091 (11) | 0.0188 (12) |
C2 | 0.0534 (15) | 0.0687 (18) | 0.115 (2) | 0.0248 (14) | 0.0083 (14) | 0.0297 (16) |
C3 | 0.0731 (19) | 0.0611 (18) | 0.131 (3) | 0.0272 (15) | 0.0004 (17) | 0.0318 (17) |
C4 | 0.086 (2) | 0.087 (2) | 0.096 (2) | 0.0542 (18) | 0.0119 (17) | 0.0250 (18) |
C5 | 0.0718 (18) | 0.129 (3) | 0.099 (2) | 0.059 (2) | 0.0362 (16) | 0.056 (2) |
C6 | 0.0661 (17) | 0.0918 (19) | 0.0852 (18) | 0.0401 (15) | 0.0324 (14) | 0.0475 (15) |
C7 | 0.0468 (14) | 0.0612 (16) | 0.0564 (14) | 0.0225 (12) | 0.0102 (11) | 0.0191 (12) |
C8 | 0.0511 (13) | 0.0499 (14) | 0.0517 (13) | 0.0227 (11) | 0.0125 (11) | 0.0162 (11) |
C9 | 0.0560 (14) | 0.0596 (15) | 0.0499 (13) | 0.0213 (12) | 0.0118 (11) | 0.0195 (12) |
C10 | 0.0697 (16) | 0.0620 (17) | 0.0854 (18) | 0.0181 (13) | 0.0119 (14) | 0.0238 (14) |
C11 | 0.0538 (14) | 0.0602 (15) | 0.0430 (12) | 0.0207 (12) | 0.0146 (11) | 0.0162 (11) |
C12 | 0.0464 (12) | 0.0570 (15) | 0.0494 (13) | 0.0213 (11) | 0.0092 (10) | 0.0209 (12) |
C13 | 0.0636 (15) | 0.0862 (19) | 0.0605 (15) | 0.0274 (14) | 0.0210 (12) | 0.0334 (14) |
C14 | 0.0695 (17) | 0.098 (2) | 0.084 (2) | 0.0190 (16) | 0.0178 (15) | 0.0577 (19) |
C15 | 0.0643 (16) | 0.0588 (17) | 0.098 (2) | 0.0155 (14) | −0.0071 (16) | 0.0352 (17) |
C16 | 0.0729 (16) | 0.0641 (18) | 0.0725 (18) | 0.0295 (14) | −0.0025 (13) | 0.0118 (14) |
C17 | 0.0756 (16) | 0.0630 (16) | 0.0530 (14) | 0.0326 (13) | 0.0099 (12) | 0.0194 (13) |
C18 | 0.0488 (13) | 0.0611 (15) | 0.0570 (14) | 0.0242 (12) | 0.0169 (11) | 0.0250 (13) |
C19 | 0.0573 (15) | 0.0679 (17) | 0.0704 (16) | 0.0283 (13) | 0.0155 (13) | 0.0097 (13) |
C20 | 0.0580 (15) | 0.0692 (17) | 0.0813 (18) | 0.0328 (14) | 0.0190 (14) | 0.0206 (15) |
C21 | 0.0491 (14) | 0.0742 (17) | 0.0753 (17) | 0.0243 (13) | 0.0185 (13) | 0.0335 (15) |
C22 | 0.0520 (14) | 0.0677 (17) | 0.0703 (16) | 0.0160 (13) | 0.0134 (12) | 0.0187 (13) |
C23 | 0.0508 (14) | 0.0576 (15) | 0.0654 (15) | 0.0201 (12) | 0.0221 (12) | 0.0221 (13) |
C24 | 0.0584 (16) | 0.108 (2) | 0.117 (2) | 0.0304 (16) | 0.0028 (16) | 0.0362 (19) |
C25 | 0.0687 (17) | 0.0681 (17) | 0.114 (2) | 0.0277 (14) | 0.0237 (16) | 0.0148 (15) |
Geometric parameters (Å, º) top
O1—C7 | 1.253 (2) | C12—C17 | 1.386 (3) |
N1—C7 | 1.371 (2) | C13—C14 | 1.380 (3) |
N1—N2 | 1.403 (2) | C13—H13 | 0.9300 |
N1—C1 | 1.422 (2) | C14—C15 | 1.368 (3) |
N2—C9 | 1.309 (2) | C14—H14 | 0.9300 |
N3—C11 | 1.335 (2) | C15—C16 | 1.366 (3) |
N3—C18 | 1.436 (2) | C15—H15 | 0.9300 |
N3—H3N | 0.8600 | C16—C17 | 1.373 (3) |
C1—C6 | 1.373 (3) | C16—H16 | 0.9300 |
C1—C2 | 1.378 (3) | C17—H17 | 0.9300 |
C2—C3 | 1.372 (3) | C18—C19 | 1.386 (3) |
C2—H2 | 0.9300 | C18—C23 | 1.388 (3) |
C3—C4 | 1.365 (3) | C19—C20 | 1.381 (3) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.361 (3) | C20—C21 | 1.377 (3) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.385 (3) | C21—C22 | 1.377 (3) |
C5—H5 | 0.9300 | C21—C24 | 1.505 (3) |
C6—H6 | 0.9300 | C22—C23 | 1.382 (3) |
C7—C8 | 1.436 (3) | C22—H22 | 0.9300 |
C8—C11 | 1.392 (3) | C23—C25 | 1.501 (3) |
C8—C9 | 1.433 (3) | C24—H24A | 0.9600 |
C9—C10 | 1.494 (3) | C24—H24B | 0.9600 |
C10—H10A | 0.9600 | C24—H24C | 0.9600 |
C10—H10B | 0.9600 | C25—H25A | 0.9600 |
C10—H10C | 0.9600 | C25—H25B | 0.9600 |
C11—C12 | 1.475 (3) | C25—H25C | 0.9600 |
C12—C13 | 1.379 (3) | ||
C7—N1—N2 | 111.97 (17) | C14—C13—C12 | 120.2 (2) |
C7—N1—C1 | 128.56 (19) | C14—C13—H13 | 119.9 |
N2—N1—C1 | 119.00 (17) | C12—C13—H13 | 119.9 |
C9—N2—N1 | 105.94 (16) | C15—C14—C13 | 120.3 (2) |
C11—N3—C18 | 131.78 (19) | C15—C14—H14 | 119.9 |
C11—N3—H3N | 114.1 | C13—C14—H14 | 119.9 |
C18—N3—H3N | 114.1 | C16—C15—C14 | 120.2 (2) |
C6—C1—C2 | 119.6 (2) | C16—C15—H15 | 119.9 |
C6—C1—N1 | 120.4 (2) | C14—C15—H15 | 119.9 |
C2—C1—N1 | 120.0 (2) | C15—C16—C17 | 120.0 (2) |
C3—C2—C1 | 119.6 (2) | C15—C16—H16 | 120.0 |
C3—C2—H2 | 120.2 | C17—C16—H16 | 120.0 |
C1—C2—H2 | 120.2 | C16—C17—C12 | 120.6 (2) |
C4—C3—C2 | 121.2 (3) | C16—C17—H17 | 119.7 |
C4—C3—H3 | 119.4 | C12—C17—H17 | 119.7 |
C2—C3—H3 | 119.4 | C19—C18—C23 | 119.8 (2) |
C5—C4—C3 | 119.2 (3) | C19—C18—N3 | 122.6 (2) |
C5—C4—H4 | 120.4 | C23—C18—N3 | 117.6 (2) |
C3—C4—H4 | 120.4 | C20—C19—C18 | 120.2 (2) |
C4—C5—C6 | 120.6 (3) | C20—C19—H19 | 119.9 |
C4—C5—H5 | 119.7 | C18—C19—H19 | 119.9 |
C6—C5—H5 | 119.7 | C21—C20—C19 | 121.1 (2) |
C1—C6—C5 | 119.8 (2) | C21—C20—H20 | 119.4 |
C1—C6—H6 | 120.1 | C19—C20—H20 | 119.4 |
C5—C6—H6 | 120.1 | C22—C21—C20 | 117.6 (2) |
O1—C7—N1 | 125.8 (2) | C22—C21—C24 | 122.1 (2) |
O1—C7—C8 | 129.00 (19) | C20—C21—C24 | 120.3 (2) |
N1—C7—C8 | 105.17 (19) | C21—C22—C23 | 123.1 (2) |
C11—C8—C9 | 131.9 (2) | C21—C22—H22 | 118.5 |
C11—C8—C7 | 122.9 (2) | C23—C22—H22 | 118.5 |
C9—C8—C7 | 104.98 (18) | C22—C23—C18 | 118.2 (2) |
N2—C9—C8 | 111.93 (19) | C22—C23—C25 | 120.3 (2) |
N2—C9—C10 | 117.8 (2) | C18—C23—C25 | 121.5 (2) |
C8—C9—C10 | 130.2 (2) | C21—C24—H24A | 109.5 |
C9—C10—H10A | 109.5 | C21—C24—H24B | 109.5 |
C9—C10—H10B | 109.5 | H24A—C24—H24B | 109.5 |
H10A—C10—H10B | 109.5 | C21—C24—H24C | 109.5 |
C9—C10—H10C | 109.5 | H24A—C24—H24C | 109.5 |
H10A—C10—H10C | 109.5 | H24B—C24—H24C | 109.5 |
H10B—C10—H10C | 109.5 | C23—C25—H25A | 109.5 |
N3—C11—C8 | 117.88 (19) | C23—C25—H25B | 109.5 |
N3—C11—C12 | 119.33 (18) | H25A—C25—H25B | 109.5 |
C8—C11—C12 | 122.69 (19) | C23—C25—H25C | 109.5 |
C13—C12—C17 | 118.8 (2) | H25A—C25—H25C | 109.5 |
C13—C12—C11 | 120.1 (2) | H25B—C25—H25C | 109.5 |
C17—C12—C11 | 121.16 (19) | ||
C7—N1—N2—C9 | 0.8 (2) | C7—C8—C11—N3 | 1.9 (3) |
C1—N1—N2—C9 | 173.61 (18) | C9—C8—C11—C12 | −0.5 (4) |
C7—N1—C1—C6 | 148.6 (2) | C7—C8—C11—C12 | −174.40 (19) |
N2—N1—C1—C6 | −22.9 (3) | N3—C11—C12—C13 | −75.1 (3) |
C7—N1—C1—C2 | −32.5 (3) | C8—C11—C12—C13 | 101.1 (2) |
N2—N1—C1—C2 | 156.0 (2) | N3—C11—C12—C17 | 104.3 (2) |
C6—C1—C2—C3 | −0.8 (4) | C8—C11—C12—C17 | −79.5 (3) |
N1—C1—C2—C3 | −179.6 (2) | C17—C12—C13—C14 | −0.5 (3) |
C1—C2—C3—C4 | −0.1 (4) | C11—C12—C13—C14 | 178.81 (19) |
C2—C3—C4—C5 | 0.7 (4) | C12—C13—C14—C15 | −0.5 (3) |
C3—C4—C5—C6 | −0.3 (4) | C13—C14—C15—C16 | 0.9 (4) |
C2—C1—C6—C5 | 1.1 (4) | C14—C15—C16—C17 | −0.3 (4) |
N1—C1—C6—C5 | 180.0 (2) | C15—C16—C17—C12 | −0.8 (3) |
C4—C5—C6—C1 | −0.5 (4) | C13—C12—C17—C16 | 1.2 (3) |
N2—N1—C7—O1 | 178.31 (19) | C11—C12—C17—C16 | −178.17 (19) |
C1—N1—C7—O1 | 6.4 (4) | C11—N3—C18—C19 | −32.7 (3) |
N2—N1—C7—C8 | −0.8 (2) | C11—N3—C18—C23 | 147.9 (2) |
C1—N1—C7—C8 | −172.76 (19) | C23—C18—C19—C20 | −1.7 (3) |
O1—C7—C8—C11 | −3.3 (4) | N3—C18—C19—C20 | 178.85 (19) |
N1—C7—C8—C11 | 175.84 (19) | C18—C19—C20—C21 | 0.6 (3) |
O1—C7—C8—C9 | −178.6 (2) | C19—C20—C21—C22 | 0.9 (3) |
N1—C7—C8—C9 | 0.5 (2) | C19—C20—C21—C24 | −179.7 (2) |
N1—N2—C9—C8 | −0.4 (2) | C20—C21—C22—C23 | −1.3 (3) |
N1—N2—C9—C10 | 179.92 (18) | C24—C21—C22—C23 | 179.3 (2) |
C11—C8—C9—N2 | −174.8 (2) | C21—C22—C23—C18 | 0.2 (3) |
C7—C8—C9—N2 | 0.0 (2) | C21—C22—C23—C25 | −178.0 (2) |
C11—C8—C9—C10 | 4.8 (4) | C19—C18—C23—C22 | 1.3 (3) |
C7—C8—C9—C10 | 179.5 (2) | N3—C18—C23—C22 | −179.21 (18) |
C18—N3—C11—C8 | −177.90 (19) | C19—C18—C23—C25 | 179.5 (2) |
C18—N3—C11—C12 | −1.5 (3) | N3—C18—C23—C25 | −1.1 (3) |
C9—C8—C11—N3 | 175.8 (2) |