Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026656/rn6061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026656/rn6061Isup2.hkl |
CCDC reference: 287693
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.121
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
1-Phenyl-3-methyl-4-benzoyl-5-pyrazolone (2.50 g, 9.0 mmol) and 4-aminotoluene (0.96 ml, 9.4 mmol) were dissolved in ethanol (35 ml) and the solution was refluxed for 6 h. The solvent was removed and the pure product was obtained upon recrystallization from a 1:1 ethanol/n-heptane mixture (35 ml) in about 75% yield. Crystals were grown from an ethanol solution. CHN elemental analysis calculated for C24H21N3O: C 78.45, H 5.76, N 11.44%; found: C 78.37, H 5.42, N 11.61%.
The C-bound H atoms were positioned geometrically [C—Haromatic = 0.93 Å and Uiso(H) = 1.2Ueq(C); C—Hmethyl = 0.96 Å and Uiso(H) = 1.5Ueq(C)], and were included in the refinement in the riding model approximation; the methyl groups were rotated for a best fit with the electron density. The N-bound H atom was located in a difference Fourier map and was refined with a distance restraint of N—H = 0.86 (1) Å. The dispalcement parameter of this H atom was also refined.
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP in SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXL97.
Fig. 1. ORTEP (Bruker, 1999) plot showing the numbering scheme of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are drawn as spheres of arbitrary radii. |
C24H21N3O | Z = 2 |
Mr = 367.44 | F(000) = 388 |
Triclinic, P1 | Dx = 1.245 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4272 (10) Å | Cell parameters from 892 reflections |
b = 11.0766 (14) Å | θ = 2.1–26.1° |
c = 13.6124 (17) Å | µ = 0.08 mm−1 |
α = 110.095 (2)° | T = 295 K |
β = 99.798 (2)° | Block, yellow |
γ = 104.067 (2)° | 0.50 × 0.45 × 0.27 mm |
V = 979.8 (2) Å3 |
Bruker SMART area-detector diffractometer | 2816 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 26.1°, θmin = 2.1° |
ω scans | h = −9→9 |
5537 measured reflections | k = −10→13 |
3811 independent reflections | l = −16→16 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0638P)2 + 0.1375P] where P = (Fo2 + 2Fc2)/3 |
3811 reflections | (Δ/σ)max = 0.001 |
259 parameters | Δρmax = 0.17 e Å−3 |
1 restraint | Δρmin = −0.15 e Å−3 |
C24H21N3O | γ = 104.067 (2)° |
Mr = 367.44 | V = 979.8 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4272 (10) Å | Mo Kα radiation |
b = 11.0766 (14) Å | µ = 0.08 mm−1 |
c = 13.6124 (17) Å | T = 295 K |
α = 110.095 (2)° | 0.50 × 0.45 × 0.27 mm |
β = 99.798 (2)° |
Bruker SMART area-detector diffractometer | 2816 reflections with I > 2σ(I) |
5537 measured reflections | Rint = 0.013 |
3811 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 1 restraint |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.17 e Å−3 |
3811 reflections | Δρmin = −0.15 e Å−3 |
259 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.49606 (16) | 1.12709 (11) | 0.23819 (9) | 0.0563 (3) | |
N1 | 0.30856 (18) | 1.09773 (12) | 0.35506 (10) | 0.0481 (3) | |
N2 | 0.24519 (19) | 1.00079 (13) | 0.39655 (10) | 0.0512 (3) | |
N3 | 0.63223 (19) | 0.91817 (13) | 0.17181 (10) | 0.0520 (3) | |
H3N | 0.611 (3) | 0.9941 (13) | 0.1732 (14) | 0.070 (5)* | |
C1 | 0.0413 (2) | 1.18365 (17) | 0.37729 (13) | 0.0580 (4) | |
H1 | −0.0309 | 1.1015 | 0.3761 | 0.070* | |
C2 | −0.0367 (3) | 1.2871 (2) | 0.38764 (14) | 0.0679 (5) | |
H2 | −0.1626 | 1.2742 | 0.3929 | 0.081* | |
C3 | 0.0701 (3) | 1.4088 (2) | 0.39029 (14) | 0.0683 (5) | |
H3 | 0.0166 | 1.4779 | 0.3970 | 0.082* | |
C4 | 0.2547 (3) | 1.42792 (18) | 0.38312 (15) | 0.0689 (5) | |
H4 | 0.3270 | 1.5104 | 0.3850 | 0.083* | |
C5 | 0.3355 (3) | 1.32616 (16) | 0.37305 (14) | 0.0587 (4) | |
H5 | 0.4623 | 1.3405 | 0.3692 | 0.070* | |
C6 | 0.2282 (2) | 1.20374 (15) | 0.36873 (11) | 0.0470 (4) | |
C7 | 0.4280 (2) | 1.06380 (15) | 0.29099 (12) | 0.0453 (3) | |
C8 | 0.4487 (2) | 0.94046 (14) | 0.29704 (11) | 0.0443 (3) | |
C9 | 0.3285 (2) | 0.90911 (15) | 0.36307 (11) | 0.0472 (3) | |
C10 | 0.2844 (3) | 0.79083 (18) | 0.39412 (15) | 0.0635 (4) | |
H10A | 0.1874 | 0.7952 | 0.4325 | 0.095* | |
H10B | 0.3996 | 0.7932 | 0.4402 | 0.095* | |
H10C | 0.2378 | 0.7079 | 0.3297 | 0.095* | |
C11 | 0.5529 (2) | 0.86998 (14) | 0.23734 (11) | 0.0440 (3) | |
C12 | 0.5688 (2) | 0.73938 (14) | 0.23876 (11) | 0.0459 (3) | |
C13 | 0.6766 (2) | 0.73512 (16) | 0.33028 (13) | 0.0544 (4) | |
H13 | 0.7367 | 0.8142 | 0.3933 | 0.065* | |
C14 | 0.6945 (3) | 0.61309 (19) | 0.32770 (15) | 0.0662 (5) | |
H14 | 0.7676 | 0.6100 | 0.3889 | 0.079* | |
C15 | 0.6043 (3) | 0.49575 (18) | 0.23468 (16) | 0.0707 (5) | |
H15 | 0.6183 | 0.4139 | 0.2329 | 0.085* | |
C16 | 0.4942 (3) | 0.49955 (17) | 0.14488 (15) | 0.0685 (5) | |
H16 | 0.4308 | 0.4198 | 0.0829 | 0.082* | |
C17 | 0.4773 (2) | 0.62065 (16) | 0.14615 (13) | 0.0561 (4) | |
H17 | 0.4040 | 0.6230 | 0.0846 | 0.067* | |
C18 | 0.7540 (2) | 0.87058 (14) | 0.10822 (12) | 0.0479 (4) | |
C19 | 0.8978 (2) | 0.82606 (18) | 0.14621 (13) | 0.0594 (4) | |
H19 | 0.9173 | 0.8249 | 0.2152 | 0.071* | |
C20 | 1.0127 (2) | 0.78317 (19) | 0.08117 (14) | 0.0634 (5) | |
H20 | 1.1072 | 0.7509 | 0.1066 | 0.076* | |
C21 | 0.9915 (2) | 0.78670 (17) | −0.02061 (13) | 0.0589 (4) | |
C22 | 0.8504 (3) | 0.83445 (17) | −0.05586 (13) | 0.0601 (4) | |
H22 | 0.8346 | 0.8391 | −0.1236 | 0.072* | |
C23 | 0.7315 (2) | 0.87566 (16) | 0.00680 (13) | 0.0530 (4) | |
H23 | 0.6360 | 0.9069 | −0.0191 | 0.064* | |
C24 | 1.1209 (3) | 0.7397 (3) | −0.08927 (18) | 0.0919 (7) | |
H24A | 1.0833 | 0.6423 | −0.1184 | 0.138* | |
H24B | 1.2526 | 0.7779 | −0.0451 | 0.138* | |
H24C | 1.1090 | 0.7691 | −0.1480 | 0.138* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0640 (7) | 0.0570 (6) | 0.0666 (7) | 0.0297 (5) | 0.0309 (6) | 0.0338 (6) |
N1 | 0.0552 (7) | 0.0450 (7) | 0.0530 (7) | 0.0243 (6) | 0.0221 (6) | 0.0212 (6) |
N2 | 0.0585 (8) | 0.0498 (7) | 0.0519 (7) | 0.0222 (6) | 0.0214 (6) | 0.0222 (6) |
N3 | 0.0606 (8) | 0.0525 (8) | 0.0539 (7) | 0.0294 (7) | 0.0240 (6) | 0.0231 (6) |
C1 | 0.0541 (10) | 0.0537 (9) | 0.0603 (10) | 0.0203 (8) | 0.0172 (8) | 0.0137 (8) |
C2 | 0.0594 (10) | 0.0784 (13) | 0.0661 (11) | 0.0385 (10) | 0.0188 (9) | 0.0175 (9) |
C3 | 0.0912 (14) | 0.0688 (12) | 0.0622 (10) | 0.0531 (11) | 0.0278 (10) | 0.0251 (9) |
C4 | 0.0909 (14) | 0.0550 (10) | 0.0794 (12) | 0.0389 (10) | 0.0384 (11) | 0.0315 (9) |
C5 | 0.0641 (10) | 0.0537 (9) | 0.0682 (11) | 0.0288 (8) | 0.0278 (9) | 0.0253 (8) |
C6 | 0.0543 (9) | 0.0455 (8) | 0.0417 (7) | 0.0235 (7) | 0.0134 (7) | 0.0130 (6) |
C7 | 0.0465 (8) | 0.0451 (8) | 0.0446 (8) | 0.0183 (6) | 0.0127 (6) | 0.0163 (6) |
C8 | 0.0481 (8) | 0.0420 (8) | 0.0429 (7) | 0.0193 (6) | 0.0110 (6) | 0.0151 (6) |
C9 | 0.0520 (9) | 0.0456 (8) | 0.0434 (8) | 0.0184 (7) | 0.0125 (7) | 0.0161 (6) |
C10 | 0.0748 (12) | 0.0592 (10) | 0.0731 (11) | 0.0294 (9) | 0.0317 (9) | 0.0358 (9) |
C11 | 0.0450 (8) | 0.0438 (8) | 0.0388 (7) | 0.0167 (6) | 0.0070 (6) | 0.0122 (6) |
C12 | 0.0487 (8) | 0.0442 (8) | 0.0467 (8) | 0.0206 (7) | 0.0164 (7) | 0.0153 (6) |
C13 | 0.0626 (10) | 0.0543 (9) | 0.0489 (8) | 0.0280 (8) | 0.0147 (7) | 0.0180 (7) |
C14 | 0.0831 (13) | 0.0764 (12) | 0.0668 (11) | 0.0493 (10) | 0.0321 (10) | 0.0399 (10) |
C15 | 0.1013 (15) | 0.0548 (10) | 0.0842 (13) | 0.0440 (10) | 0.0533 (12) | 0.0354 (10) |
C16 | 0.0928 (14) | 0.0427 (9) | 0.0646 (11) | 0.0198 (9) | 0.0331 (10) | 0.0116 (8) |
C17 | 0.0623 (10) | 0.0503 (9) | 0.0483 (9) | 0.0170 (8) | 0.0141 (7) | 0.0129 (7) |
C18 | 0.0496 (9) | 0.0430 (8) | 0.0466 (8) | 0.0148 (7) | 0.0142 (7) | 0.0127 (6) |
C19 | 0.0546 (10) | 0.0800 (12) | 0.0439 (8) | 0.0287 (9) | 0.0127 (7) | 0.0210 (8) |
C20 | 0.0520 (10) | 0.0806 (12) | 0.0556 (10) | 0.0303 (9) | 0.0130 (8) | 0.0201 (9) |
C21 | 0.0515 (9) | 0.0625 (10) | 0.0502 (9) | 0.0155 (8) | 0.0158 (7) | 0.0096 (8) |
C22 | 0.0642 (11) | 0.0679 (11) | 0.0461 (9) | 0.0170 (9) | 0.0187 (8) | 0.0220 (8) |
C23 | 0.0544 (9) | 0.0530 (9) | 0.0548 (9) | 0.0188 (7) | 0.0155 (7) | 0.0243 (7) |
C24 | 0.0848 (15) | 0.1216 (19) | 0.0731 (13) | 0.0455 (13) | 0.0412 (12) | 0.0265 (13) |
O1—C7 | 1.2496 (17) | C11—C12 | 1.486 (2) |
N1—C7 | 1.3741 (18) | C12—C13 | 1.384 (2) |
N1—N2 | 1.3983 (17) | C12—C17 | 1.384 (2) |
N1—C6 | 1.4137 (18) | C13—C14 | 1.379 (2) |
N2—C9 | 1.3057 (18) | C13—H13 | 0.9300 |
N3—C11 | 1.3345 (19) | C14—C15 | 1.378 (3) |
N3—C18 | 1.4246 (19) | C14—H14 | 0.9300 |
N3—H3N | 0.886 (9) | C15—C16 | 1.370 (3) |
C1—C6 | 1.382 (2) | C15—H15 | 0.9300 |
C1—C2 | 1.381 (2) | C16—C17 | 1.372 (2) |
C1—H1 | 0.9300 | C16—H16 | 0.9300 |
C2—C3 | 1.373 (3) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—C19 | 1.377 (2) |
C3—C4 | 1.361 (3) | C18—C23 | 1.384 (2) |
C3—H3 | 0.9300 | C19—C20 | 1.379 (2) |
C4—C5 | 1.378 (2) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.383 (2) |
C5—C6 | 1.372 (2) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—C22 | 1.371 (2) |
C7—C8 | 1.439 (2) | C21—C24 | 1.511 (2) |
C8—C11 | 1.3933 (19) | C22—C23 | 1.379 (2) |
C8—C9 | 1.436 (2) | C22—H22 | 0.9300 |
C9—C10 | 1.490 (2) | C23—H23 | 0.9300 |
C10—H10A | 0.9600 | C24—H24A | 0.9600 |
C10—H10B | 0.9600 | C24—H24B | 0.9600 |
C10—H10C | 0.9600 | C24—H24C | 0.9600 |
C7—N1—N2 | 112.07 (11) | C13—C12—C17 | 119.61 (14) |
C7—N1—C6 | 127.47 (12) | C13—C12—C11 | 121.08 (13) |
N2—N1—C6 | 119.82 (12) | C17—C12—C11 | 119.30 (13) |
C9—N2—N1 | 106.55 (12) | C14—C13—C12 | 119.71 (15) |
C11—N3—C18 | 129.25 (13) | C14—C13—H13 | 120.1 |
C11—N3—H3N | 113.4 (12) | C12—C13—H13 | 120.1 |
C18—N3—H3N | 117.1 (12) | C15—C14—C13 | 120.18 (17) |
C6—C1—C2 | 119.15 (17) | C15—C14—H14 | 119.9 |
C6—C1—H1 | 120.4 | C13—C14—H14 | 119.9 |
C2—C1—H1 | 120.4 | C16—C15—C14 | 120.08 (16) |
C3—C2—C1 | 120.55 (17) | C16—C15—H15 | 120.0 |
C3—C2—H2 | 119.7 | C14—C15—H15 | 120.0 |
C1—C2—H2 | 119.7 | C15—C16—C17 | 120.20 (16) |
C4—C3—C2 | 119.74 (16) | C15—C16—H16 | 119.9 |
C4—C3—H3 | 120.1 | C17—C16—H16 | 119.9 |
C2—C3—H3 | 120.1 | C16—C17—C12 | 120.20 (16) |
C3—C4—C5 | 120.64 (18) | C16—C17—H17 | 119.9 |
C3—C4—H4 | 119.7 | C12—C17—H17 | 119.9 |
C5—C4—H4 | 119.7 | C19—C18—C23 | 119.31 (14) |
C6—C5—C4 | 119.76 (17) | C19—C18—N3 | 122.31 (14) |
C6—C5—H5 | 120.1 | C23—C18—N3 | 118.31 (14) |
C4—C5—H5 | 120.1 | C18—C19—C20 | 119.45 (15) |
C5—C6—C1 | 120.14 (14) | C18—C19—H19 | 120.3 |
C5—C6—N1 | 119.90 (14) | C20—C19—H19 | 120.3 |
C1—C6—N1 | 119.96 (14) | C19—C20—C21 | 122.01 (16) |
O1—C7—N1 | 125.94 (13) | C19—C20—H20 | 119.0 |
O1—C7—C8 | 129.45 (13) | C21—C20—H20 | 119.0 |
N1—C7—C8 | 104.59 (12) | C22—C21—C20 | 117.60 (15) |
C11—C8—C9 | 132.52 (13) | C22—C21—C24 | 121.87 (17) |
C11—C8—C7 | 121.77 (13) | C20—C21—C24 | 120.53 (17) |
C9—C8—C7 | 105.39 (12) | C21—C22—C23 | 121.50 (15) |
N2—C9—C8 | 111.33 (13) | C21—C22—H22 | 119.3 |
N2—C9—C10 | 118.34 (14) | C23—C22—H22 | 119.3 |
C8—C9—C10 | 130.31 (14) | C22—C23—C18 | 120.09 (15) |
C9—C10—H10A | 109.5 | C22—C23—H23 | 120.0 |
C9—C10—H10B | 109.5 | C18—C23—H23 | 120.0 |
H10A—C10—H10B | 109.5 | C21—C24—H24A | 109.5 |
C9—C10—H10C | 109.5 | C21—C24—H24B | 109.5 |
H10A—C10—H10C | 109.5 | H24A—C24—H24B | 109.5 |
H10B—C10—H10C | 109.5 | C21—C24—H24C | 109.5 |
N3—C11—C8 | 118.41 (13) | H24A—C24—H24C | 109.5 |
N3—C11—C12 | 118.92 (12) | H24B—C24—H24C | 109.5 |
C8—C11—C12 | 122.56 (13) | ||
C7—N1—N2—C9 | 2.34 (16) | C18—N3—C11—C12 | −8.0 (2) |
C6—N1—N2—C9 | 173.82 (13) | C9—C8—C11—N3 | 171.34 (15) |
C6—C1—C2—C3 | −0.5 (3) | C7—C8—C11—N3 | −1.1 (2) |
C1—C2—C3—C4 | −0.3 (3) | C9—C8—C11—C12 | −4.8 (2) |
C2—C3—C4—C5 | 0.1 (3) | C7—C8—C11—C12 | −177.26 (13) |
C3—C4—C5—C6 | 0.9 (3) | N3—C11—C12—C13 | 113.28 (16) |
C4—C5—C6—C1 | −1.7 (2) | C8—C11—C12—C13 | −70.6 (2) |
C4—C5—C6—N1 | 178.06 (15) | N3—C11—C12—C17 | −65.4 (2) |
C2—C1—C6—C5 | 1.5 (2) | C8—C11—C12—C17 | 110.76 (17) |
C2—C1—C6—N1 | −178.26 (14) | C17—C12—C13—C14 | 1.1 (2) |
C7—N1—C6—C5 | −38.0 (2) | C11—C12—C13—C14 | −177.57 (15) |
N2—N1—C6—C5 | 151.93 (14) | C12—C13—C14—C15 | −0.4 (3) |
C7—N1—C6—C1 | 141.71 (16) | C13—C14—C15—C16 | −1.0 (3) |
N2—N1—C6—C1 | −28.3 (2) | C14—C15—C16—C17 | 1.7 (3) |
N2—N1—C7—O1 | 175.35 (14) | C15—C16—C17—C12 | −1.0 (3) |
C6—N1—C7—O1 | 4.7 (2) | C13—C12—C17—C16 | −0.4 (2) |
N2—N1—C7—C8 | −2.96 (16) | C11—C12—C17—C16 | 178.32 (15) |
C6—N1—C7—C8 | −173.64 (13) | C11—N3—C18—C19 | −40.0 (2) |
O1—C7—C8—C11 | −1.6 (2) | C11—N3—C18—C23 | 143.00 (16) |
N1—C7—C8—C11 | 176.62 (13) | C23—C18—C19—C20 | −2.1 (3) |
O1—C7—C8—C9 | −175.83 (15) | N3—C18—C19—C20 | −179.02 (15) |
N1—C7—C8—C9 | 2.39 (15) | C18—C19—C20—C21 | 1.7 (3) |
N1—N2—C9—C8 | −0.66 (16) | C19—C20—C21—C22 | −0.2 (3) |
N1—N2—C9—C10 | −179.09 (13) | C19—C20—C21—C24 | 179.61 (18) |
C11—C8—C9—N2 | −174.45 (15) | C20—C21—C22—C23 | −1.0 (3) |
C7—C8—C9—N2 | −1.11 (17) | C24—C21—C22—C23 | 179.24 (17) |
C11—C8—C9—C10 | 3.7 (3) | C21—C22—C23—C18 | 0.6 (3) |
C7—C8—C9—C10 | 177.08 (16) | C19—C18—C23—C22 | 1.0 (2) |
C18—N3—C11—C8 | 175.70 (14) | N3—C18—C23—C22 | 178.03 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O1 | 0.89 (1) | 1.91 (1) | 2.6845 (16) | 144 (2) |
Experimental details
Crystal data | |
Chemical formula | C24H21N3O |
Mr | 367.44 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.4272 (10), 11.0766 (14), 13.6124 (17) |
α, β, γ (°) | 110.095 (2), 99.798 (2), 104.067 (2) |
V (Å3) | 979.8 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.45 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5537, 3811, 2816 |
Rint | 0.013 |
(sin θ/λ)max (Å−1) | 0.620 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.121, 1.01 |
No. of reflections | 3811 |
No. of parameters | 259 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Computer programs: SMART (Bruker, 1999), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP in SHELXTL (Bruker, 1999), SHELXL97.
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5-Methyl-2-phenyl-4-[(Z)-(2-tolylamino)phenylmethylene]pyrazol-3(2H)-one exists as a monomeric compound whose NH unit is linked to the C═O unit by a short [2.695 (2) Å] hydrogen bond (Bao et al., 2004). The isomeric title compound, (I) (Fig. 1), displays a somewhat shorter hydrogen bond [2.685 (2) Å]; otherwise, there are no significant differences between the two isomers. The two hydrogen bonds are slightly shorter than that found in 4-[(phenyl)phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3-one [2.704 (2) Å; Ma, 2005].