Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051033/hb2585sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051033/hb2585Isup2.hkl |
CCDC reference: 667426
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.063
- wR factor = 0.144
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.139 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Bao et al. (2004); Ma (2005); Ma et al. (2006a,b).
1-Phenyl-3-methyl-4-benzoyl-5-pyrazolone (1.60 g, 5.8 mm mol) and 2,4-dimethylaniline (0.73 g, 6.0 mm mol) were dissolved in ethanol (35 ml); formic acid (0.5 ml) was added to catalyse the reaction. The solution was heated under reflux for 8 h. The solvent was removed and the pure product obtained upon recrystallization from a 1:1 ethanol/n-heptane mixture in 80% yield. Yellow blocks of (I) were grown from an ethanol solution of the compound. Elemental analysis calculated for C25H23N3O: C 79.29, H 9.15, N 11.56%; found: C 79.40, H 9.32, N 11.35%.
The H atoms were placed in calculated positions (C—H = 0.93–0.96 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).
The title compound, (I) (Fig. 1) has two methyl substituents in the 2,5-dimethylphenylamino portion of the molecule; the general features are similar to those found in the analogous 2-tolylamino (Bao et al., 2004), 2,4-dimethylphenylamino(Ma et al., 2006b) and 4-tolylamino (Ma, 2005) derivatives. Compound (I) can be used to chelate to a divalent transition metal (Ma et al., 2006a). In both asymmetric molecules of (I), an intramolecular N—H···O hydrogen bond occurs (Table 1).
For related literature, see: Bao et al. (2004); Ma (2005); Ma et al. (2006a,b).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. Vew of the molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius. |
C25H23N3O | F(000) = 1616 |
Mr = 381.46 | Dx = 1.224 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1791 reflections |
a = 24.011 (3) Å | θ = 2.5–17.0° |
b = 14.2004 (16) Å | µ = 0.08 mm−1 |
c = 12.5487 (15) Å | T = 293 K |
β = 104.601 (2)° | Block, yellow |
V = 4140.5 (9) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 8 |
Bruker SMART CCD diffractometer | 7291 independent reflections |
Radiation source: fine-focus sealed tube | 3103 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.139 |
ω scans | θmax = 25.0°, θmin = 0.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −28→28 |
Tmin = 0.982, Tmax = 0.992 | k = −14→16 |
26490 measured reflections | l = −14→14 |
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)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.0394P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.85 | (Δ/σ)max < 0.001 |
7291 reflections | Δρmax = 0.19 e Å−3 |
530 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Bruker, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0020 (3) |
C25H23N3O | V = 4140.5 (9) Å3 |
Mr = 381.46 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 24.011 (3) Å | µ = 0.08 mm−1 |
b = 14.2004 (16) Å | T = 293 K |
c = 12.5487 (15) Å | 0.30 × 0.20 × 0.10 mm |
β = 104.601 (2)° |
Bruker SMART CCD diffractometer | 7291 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 3103 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.992 | Rint = 0.139 |
26490 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 0.85 | Δρmax = 0.19 e Å−3 |
7291 reflections | Δρmin = −0.19 e Å−3 |
530 parameters |
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 | ||
O1 | 0.67019 (10) | 0.51803 (16) | 0.0567 (2) | 0.0646 (8) | |
N1 | 0.63486 (11) | 0.34429 (19) | −0.0131 (2) | 0.0504 (8) | |
H1 | 0.6535 | 0.3959 | −0.0142 | 0.061* | |
N2 | 0.60746 (12) | 0.5833 (2) | 0.1519 (2) | 0.0510 (8) | |
N3 | 0.55672 (12) | 0.5571 (2) | 0.1796 (2) | 0.0546 (8) | |
C1 | 0.67171 (18) | 0.0015 (3) | −0.0476 (4) | 0.0890 (14) | |
H1A | 0.6670 | 0.0004 | 0.0261 | 0.133* | |
H1B | 0.7068 | −0.0300 | −0.0495 | 0.133* | |
H1C | 0.6398 | −0.0299 | −0.0961 | 0.133* | |
C2 | 0.67414 (15) | 0.1026 (3) | −0.0846 (3) | 0.0576 (11) | |
C3 | 0.69913 (15) | 0.1257 (3) | −0.1693 (3) | 0.0629 (12) | |
H3 | 0.7136 | 0.0782 | −0.2058 | 0.075* | |
C4 | 0.70298 (15) | 0.2191 (3) | −0.2008 (3) | 0.0635 (11) | |
H4 | 0.7208 | 0.2328 | −0.2567 | 0.076* | |
C5 | 0.68098 (14) | 0.2915 (3) | −0.1508 (3) | 0.0479 (9) | |
C6 | 0.65489 (14) | 0.2684 (2) | −0.0663 (3) | 0.0443 (9) | |
C7 | 0.65241 (14) | 0.1753 (2) | −0.0341 (3) | 0.0512 (10) | |
H7 | 0.6356 | 0.1614 | 0.0231 | 0.061* | |
C8 | 0.68520 (16) | 0.3915 (3) | −0.1861 (3) | 0.0683 (12) | |
H8A | 0.7030 | 0.3931 | −0.2465 | 0.102* | |
H8B | 0.7079 | 0.4272 | −0.1256 | 0.102* | |
H8C | 0.6473 | 0.4183 | −0.2088 | 0.102* | |
C9 | 0.59229 (13) | 0.3519 (2) | 0.0385 (3) | 0.0400 (8) | |
C10 | 0.55344 (14) | 0.2711 (2) | 0.0405 (3) | 0.0389 (8) | |
C11 | 0.55606 (14) | 0.2278 (2) | 0.1404 (3) | 0.0481 (9) | |
H11 | 0.5809 | 0.2507 | 0.2045 | 0.058* | |
C12 | 0.52173 (17) | 0.1507 (3) | 0.1446 (3) | 0.0642 (11) | |
H12 | 0.5236 | 0.1212 | 0.2117 | 0.077* | |
C13 | 0.48491 (17) | 0.1174 (3) | 0.0506 (4) | 0.0640 (12) | |
H13 | 0.4622 | 0.0649 | 0.0540 | 0.077* | |
C14 | 0.48122 (16) | 0.1607 (3) | −0.0481 (3) | 0.0641 (11) | |
H14 | 0.4552 | 0.1387 | −0.1112 | 0.077* | |
C15 | 0.51585 (15) | 0.2367 (3) | −0.0544 (3) | 0.0536 (10) | |
H15 | 0.5140 | 0.2650 | −0.1220 | 0.064* | |
C16 | 0.58641 (13) | 0.4375 (2) | 0.0878 (3) | 0.0415 (9) | |
C17 | 0.62622 (15) | 0.5138 (2) | 0.0943 (3) | 0.0470 (9) | |
C18 | 0.54434 (14) | 0.4717 (2) | 0.1421 (3) | 0.0448 (9) | |
C19 | 0.49001 (14) | 0.4262 (2) | 0.1543 (3) | 0.0632 (11) | |
H19A | 0.4990 | 0.3811 | 0.2132 | 0.095* | |
H19B | 0.4714 | 0.3948 | 0.0870 | 0.095* | |
H19C | 0.4648 | 0.4734 | 0.1707 | 0.095* | |
C20 | 0.63215 (15) | 0.6723 (2) | 0.1862 (3) | 0.0500 (10) | |
C21 | 0.67085 (16) | 0.7118 (3) | 0.1349 (3) | 0.0685 (12) | |
H21 | 0.6816 | 0.6793 | 0.0789 | 0.082* | |
C22 | 0.69358 (19) | 0.7996 (3) | 0.1665 (4) | 0.0880 (15) | |
H22 | 0.7191 | 0.8270 | 0.1308 | 0.106* | |
C23 | 0.67845 (18) | 0.8466 (3) | 0.2510 (4) | 0.0817 (14) | |
H23 | 0.6942 | 0.9055 | 0.2729 | 0.098* | |
C24 | 0.64080 (19) | 0.8076 (3) | 0.3025 (3) | 0.0741 (13) | |
H24 | 0.6307 | 0.8400 | 0.3592 | 0.089* | |
C25 | 0.61707 (15) | 0.7188 (3) | 0.2709 (3) | 0.0564 (10) | |
H25 | 0.5915 | 0.6917 | 0.3066 | 0.068* | |
O2 | 0.82990 (11) | −0.02049 (16) | 0.8951 (2) | 0.0628 (7) | |
N4 | 0.86655 (12) | 0.1502 (2) | 0.8538 (2) | 0.0522 (8) | |
H4A | 0.8474 | 0.0989 | 0.8351 | 0.063* | |
N5 | 0.89146 (12) | −0.0833 (2) | 1.0548 (2) | 0.0500 (8) | |
N6 | 0.94280 (13) | −0.0567 (2) | 1.1309 (2) | 0.0553 (8) | |
C26 | 0.81578 (17) | 0.1054 (3) | 0.6290 (3) | 0.0744 (12) | |
H26A | 0.8017 | 0.1058 | 0.5503 | 0.112* | |
H26B | 0.7893 | 0.0717 | 0.6610 | 0.112* | |
H26C | 0.8527 | 0.0751 | 0.6489 | 0.112* | |
C27 | 0.82146 (15) | 0.2048 (3) | 0.6711 (3) | 0.0528 (10) | |
C28 | 0.80112 (16) | 0.2794 (4) | 0.6015 (3) | 0.0674 (12) | |
H28 | 0.7840 | 0.2668 | 0.5278 | 0.081* | |
C29 | 0.80515 (16) | 0.3718 (3) | 0.6370 (4) | 0.0669 (12) | |
H29 | 0.7915 | 0.4200 | 0.5871 | 0.080* | |
C30 | 0.82946 (15) | 0.3925 (3) | 0.7463 (4) | 0.0592 (11) | |
C31 | 0.84949 (14) | 0.3184 (3) | 0.8175 (3) | 0.0532 (10) | |
H31 | 0.8652 | 0.3310 | 0.8917 | 0.064* | |
C32 | 0.84670 (14) | 0.2270 (3) | 0.7812 (3) | 0.0466 (9) | |
C33 | 0.83310 (18) | 0.4922 (3) | 0.7875 (4) | 0.0928 (15) | |
H33A | 0.8315 | 0.4926 | 0.8632 | 0.139* | |
H33B | 0.8014 | 0.5278 | 0.7442 | 0.139* | |
H33C | 0.8687 | 0.5198 | 0.7815 | 0.139* | |
C34 | 0.90941 (15) | 0.1428 (2) | 0.9461 (3) | 0.0433 (9) | |
C35 | 0.94845 (13) | 0.2243 (2) | 0.9825 (3) | 0.0400 (8) | |
C36 | 0.98698 (15) | 0.2547 (3) | 0.9240 (3) | 0.0545 (10) | |
H36 | 0.9895 | 0.2228 | 0.8606 | 0.065* | |
C37 | 1.02148 (16) | 0.3316 (3) | 0.9590 (3) | 0.0680 (12) | |
H37 | 1.0474 | 0.3516 | 0.9198 | 0.082* | |
C38 | 1.01742 (18) | 0.3792 (3) | 1.0532 (4) | 0.0708 (12) | |
H38 | 1.0401 | 0.4321 | 1.0763 | 0.085* | |
C39 | 0.98041 (18) | 0.3490 (3) | 1.1119 (3) | 0.0659 (11) | |
H39 | 0.9781 | 0.3810 | 1.1753 | 0.079* | |
C40 | 0.94632 (15) | 0.2714 (3) | 1.0781 (3) | 0.0508 (10) | |
H40 | 0.9217 | 0.2504 | 1.1195 | 0.061* | |
C41 | 0.91444 (14) | 0.0598 (2) | 1.0050 (3) | 0.0418 (9) | |
C42 | 0.95604 (14) | 0.0279 (3) | 1.1014 (3) | 0.0451 (9) | |
C43 | 0.87312 (16) | −0.0160 (2) | 0.9754 (3) | 0.0483 (9) | |
C44 | 1.01056 (14) | 0.0730 (2) | 1.1639 (3) | 0.0617 (11) | |
H44A | 1.0335 | 0.0276 | 1.2127 | 0.093* | |
H44B | 1.0018 | 0.1248 | 1.2060 | 0.093* | |
H44C | 1.0316 | 0.0955 | 1.1133 | 0.093* | |
C45 | 0.86489 (16) | −0.1701 (3) | 1.0705 (3) | 0.0504 (10) | |
C46 | 0.82352 (18) | −0.2102 (3) | 0.9886 (3) | 0.0704 (12) | |
H46 | 0.8125 | −0.1809 | 0.9202 | 0.084* | |
C47 | 0.79789 (19) | −0.2935 (3) | 1.0058 (4) | 0.0866 (14) | |
H47 | 0.7699 | −0.3207 | 0.9492 | 0.104* | |
C48 | 0.8140 (2) | −0.3363 (3) | 1.1072 (5) | 0.0890 (15) | |
H48 | 0.7966 | −0.3923 | 1.1194 | 0.107* | |
C49 | 0.8553 (2) | −0.2972 (3) | 1.1897 (4) | 0.0750 (13) | |
H49 | 0.8665 | −0.3270 | 1.2577 | 0.090* | |
C50 | 0.88070 (15) | −0.2128 (3) | 1.1725 (3) | 0.0566 (10) | |
H50 | 0.9083 | −0.1852 | 1.2294 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0691 (18) | 0.0505 (17) | 0.088 (2) | −0.0123 (14) | 0.0454 (16) | −0.0124 (14) |
N1 | 0.0615 (19) | 0.0379 (18) | 0.061 (2) | −0.0102 (16) | 0.0330 (16) | −0.0075 (15) |
N2 | 0.058 (2) | 0.043 (2) | 0.059 (2) | −0.0052 (16) | 0.0281 (16) | −0.0092 (16) |
N3 | 0.062 (2) | 0.050 (2) | 0.060 (2) | −0.0035 (17) | 0.0301 (17) | −0.0097 (16) |
C1 | 0.087 (3) | 0.053 (3) | 0.131 (4) | −0.008 (2) | 0.033 (3) | −0.014 (3) |
C2 | 0.043 (2) | 0.049 (3) | 0.079 (3) | −0.003 (2) | 0.013 (2) | −0.017 (2) |
C3 | 0.053 (3) | 0.068 (3) | 0.070 (3) | 0.007 (2) | 0.020 (2) | −0.031 (2) |
C4 | 0.049 (2) | 0.090 (4) | 0.054 (3) | 0.005 (2) | 0.017 (2) | −0.013 (3) |
C5 | 0.048 (2) | 0.056 (3) | 0.044 (2) | 0.000 (2) | 0.0192 (18) | −0.001 (2) |
C6 | 0.048 (2) | 0.042 (2) | 0.046 (2) | −0.0021 (19) | 0.0170 (18) | −0.0108 (19) |
C7 | 0.053 (2) | 0.043 (3) | 0.060 (3) | −0.005 (2) | 0.0197 (19) | −0.009 (2) |
C8 | 0.072 (3) | 0.075 (3) | 0.067 (3) | −0.007 (2) | 0.035 (2) | 0.006 (2) |
C9 | 0.041 (2) | 0.044 (2) | 0.037 (2) | −0.0027 (18) | 0.0140 (17) | 0.0034 (18) |
C10 | 0.043 (2) | 0.041 (2) | 0.035 (2) | 0.0013 (18) | 0.0147 (17) | −0.0015 (17) |
C11 | 0.057 (2) | 0.048 (2) | 0.038 (2) | −0.005 (2) | 0.0100 (18) | 0.0047 (19) |
C12 | 0.078 (3) | 0.064 (3) | 0.059 (3) | −0.006 (2) | 0.032 (2) | 0.012 (2) |
C13 | 0.072 (3) | 0.041 (3) | 0.088 (3) | −0.016 (2) | 0.037 (3) | −0.005 (2) |
C14 | 0.061 (3) | 0.063 (3) | 0.065 (3) | −0.019 (2) | 0.011 (2) | −0.018 (2) |
C15 | 0.059 (3) | 0.055 (3) | 0.046 (2) | −0.006 (2) | 0.013 (2) | 0.002 (2) |
C16 | 0.044 (2) | 0.042 (2) | 0.042 (2) | −0.0031 (19) | 0.0165 (17) | 0.0012 (18) |
C17 | 0.051 (2) | 0.043 (2) | 0.052 (2) | −0.0003 (19) | 0.0220 (19) | −0.0030 (19) |
C18 | 0.054 (2) | 0.037 (2) | 0.047 (2) | −0.0014 (19) | 0.0189 (19) | −0.0022 (18) |
C19 | 0.065 (3) | 0.056 (3) | 0.081 (3) | −0.003 (2) | 0.040 (2) | −0.007 (2) |
C20 | 0.056 (2) | 0.036 (2) | 0.057 (3) | −0.0055 (19) | 0.012 (2) | −0.0115 (19) |
C21 | 0.085 (3) | 0.042 (3) | 0.087 (3) | −0.016 (2) | 0.039 (3) | −0.015 (2) |
C22 | 0.103 (4) | 0.053 (3) | 0.120 (4) | −0.020 (3) | 0.051 (3) | −0.015 (3) |
C23 | 0.070 (3) | 0.053 (3) | 0.118 (4) | −0.008 (3) | 0.017 (3) | −0.016 (3) |
C24 | 0.081 (3) | 0.057 (3) | 0.075 (3) | 0.009 (3) | 0.003 (3) | −0.025 (2) |
C25 | 0.061 (3) | 0.050 (3) | 0.057 (3) | 0.002 (2) | 0.013 (2) | −0.008 (2) |
O2 | 0.0699 (18) | 0.0556 (18) | 0.0517 (16) | −0.0130 (14) | −0.0052 (14) | 0.0022 (14) |
N4 | 0.064 (2) | 0.042 (2) | 0.0416 (19) | −0.0072 (17) | −0.0027 (16) | 0.0000 (16) |
N5 | 0.055 (2) | 0.044 (2) | 0.0463 (19) | −0.0075 (17) | 0.0047 (16) | 0.0042 (16) |
N6 | 0.061 (2) | 0.049 (2) | 0.048 (2) | −0.0061 (17) | −0.0022 (16) | 0.0074 (16) |
C26 | 0.077 (3) | 0.094 (4) | 0.050 (3) | −0.004 (3) | 0.011 (2) | −0.009 (2) |
C27 | 0.045 (2) | 0.071 (3) | 0.040 (2) | −0.003 (2) | 0.0070 (18) | 0.006 (2) |
C28 | 0.052 (3) | 0.106 (4) | 0.043 (3) | −0.001 (3) | 0.010 (2) | 0.016 (3) |
C29 | 0.051 (3) | 0.078 (4) | 0.067 (3) | 0.008 (2) | 0.007 (2) | 0.038 (3) |
C30 | 0.039 (2) | 0.054 (3) | 0.083 (3) | −0.002 (2) | 0.013 (2) | 0.018 (3) |
C31 | 0.052 (2) | 0.051 (3) | 0.052 (2) | −0.001 (2) | 0.0031 (19) | 0.010 (2) |
C32 | 0.047 (2) | 0.047 (3) | 0.044 (2) | −0.003 (2) | 0.0084 (18) | 0.011 (2) |
C33 | 0.085 (3) | 0.052 (3) | 0.131 (4) | −0.001 (3) | 0.007 (3) | 0.023 (3) |
C34 | 0.053 (2) | 0.041 (2) | 0.036 (2) | −0.0023 (19) | 0.0106 (18) | −0.0080 (19) |
C35 | 0.044 (2) | 0.037 (2) | 0.037 (2) | 0.0039 (18) | 0.0072 (17) | −0.0008 (17) |
C36 | 0.058 (3) | 0.057 (3) | 0.051 (2) | −0.005 (2) | 0.018 (2) | −0.004 (2) |
C37 | 0.066 (3) | 0.070 (3) | 0.068 (3) | −0.019 (2) | 0.018 (2) | 0.012 (2) |
C38 | 0.079 (3) | 0.047 (3) | 0.075 (3) | −0.015 (2) | −0.003 (3) | 0.001 (2) |
C39 | 0.084 (3) | 0.055 (3) | 0.057 (3) | −0.010 (2) | 0.013 (2) | −0.015 (2) |
C40 | 0.061 (2) | 0.049 (3) | 0.041 (2) | −0.006 (2) | 0.0116 (18) | −0.0087 (19) |
C41 | 0.047 (2) | 0.038 (2) | 0.040 (2) | −0.0021 (19) | 0.0093 (17) | −0.0017 (18) |
C42 | 0.048 (2) | 0.046 (2) | 0.039 (2) | 0.000 (2) | 0.0072 (18) | −0.0006 (19) |
C43 | 0.055 (3) | 0.043 (2) | 0.043 (2) | 0.000 (2) | 0.005 (2) | 0.001 (2) |
C44 | 0.059 (3) | 0.055 (3) | 0.060 (3) | −0.003 (2) | −0.006 (2) | 0.004 (2) |
C45 | 0.055 (2) | 0.043 (2) | 0.056 (3) | −0.004 (2) | 0.021 (2) | 0.007 (2) |
C46 | 0.088 (3) | 0.048 (3) | 0.070 (3) | −0.023 (3) | 0.010 (3) | 0.004 (2) |
C47 | 0.092 (4) | 0.061 (3) | 0.100 (4) | −0.025 (3) | 0.013 (3) | 0.002 (3) |
C48 | 0.075 (3) | 0.054 (3) | 0.140 (5) | −0.012 (3) | 0.032 (3) | 0.027 (3) |
C49 | 0.078 (3) | 0.057 (3) | 0.097 (4) | 0.009 (3) | 0.036 (3) | 0.031 (3) |
C50 | 0.065 (3) | 0.047 (3) | 0.060 (3) | 0.003 (2) | 0.018 (2) | 0.007 (2) |
O1—C17 | 1.261 (4) | O2—C43 | 1.253 (4) |
N1—C9 | 1.345 (4) | N4—C34 | 1.346 (4) |
N1—C6 | 1.413 (4) | N4—C32 | 1.424 (4) |
N1—H1 | 0.8609 | N4—H4A | 0.8615 |
N2—C17 | 1.365 (4) | N5—C43 | 1.370 (4) |
N2—N3 | 1.399 (3) | N5—N6 | 1.407 (3) |
N2—C20 | 1.415 (4) | N5—C45 | 1.425 (4) |
N3—C18 | 1.308 (4) | N6—C42 | 1.320 (4) |
C1—C2 | 1.514 (5) | C26—C27 | 1.501 (5) |
C1—H1A | 0.9600 | C26—H26A | 0.9600 |
C1—H1B | 0.9600 | C26—H26B | 0.9600 |
C1—H1C | 0.9600 | C26—H26C | 0.9600 |
C2—C7 | 1.380 (4) | C27—C28 | 1.381 (5) |
C2—C3 | 1.386 (5) | C27—C32 | 1.398 (4) |
C3—C4 | 1.393 (5) | C28—C29 | 1.381 (5) |
C3—H3 | 0.9300 | C28—H28 | 0.9300 |
C4—C5 | 1.378 (5) | C29—C30 | 1.381 (5) |
C4—H4 | 0.9300 | C29—H29 | 0.9300 |
C5—C6 | 1.400 (4) | C30—C31 | 1.385 (5) |
C5—C8 | 1.498 (5) | C30—C33 | 1.501 (5) |
C6—C7 | 1.389 (4) | C31—C32 | 1.372 (5) |
C7—H7 | 0.9300 | C31—H31 | 0.9300 |
C8—H8A | 0.9600 | C33—H33A | 0.9600 |
C8—H8B | 0.9600 | C33—H33B | 0.9600 |
C8—H8C | 0.9600 | C33—H33C | 0.9600 |
C9—C16 | 1.389 (4) | C34—C41 | 1.382 (4) |
C9—C10 | 1.483 (4) | C34—C35 | 1.486 (4) |
C10—C11 | 1.383 (4) | C35—C40 | 1.386 (4) |
C10—C15 | 1.388 (4) | C35—C36 | 1.387 (4) |
C11—C12 | 1.380 (4) | C36—C37 | 1.374 (5) |
C11—H11 | 0.9300 | C36—H36 | 0.9300 |
C12—C13 | 1.368 (5) | C37—C38 | 1.386 (5) |
C12—H12 | 0.9300 | C37—H37 | 0.9300 |
C13—C14 | 1.366 (5) | C38—C39 | 1.359 (5) |
C13—H13 | 0.9300 | C38—H38 | 0.9300 |
C14—C15 | 1.378 (5) | C39—C40 | 1.375 (5) |
C14—H14 | 0.9300 | C39—H39 | 0.9300 |
C15—H15 | 0.9300 | C40—H40 | 0.9300 |
C16—C17 | 1.433 (4) | C41—C42 | 1.434 (4) |
C16—C18 | 1.437 (4) | C41—C43 | 1.447 (4) |
C18—C19 | 1.498 (4) | C42—C44 | 1.490 (4) |
C19—H19A | 0.9600 | C44—H44A | 0.9600 |
C19—H19B | 0.9600 | C44—H44B | 0.9600 |
C19—H19C | 0.9600 | C44—H44C | 0.9600 |
C20—C25 | 1.375 (4) | C45—C46 | 1.362 (5) |
C20—C21 | 1.377 (5) | C45—C50 | 1.380 (4) |
C21—C22 | 1.379 (5) | C46—C47 | 1.375 (5) |
C21—H21 | 0.9300 | C46—H46 | 0.9300 |
C22—C23 | 1.378 (5) | C47—C48 | 1.375 (6) |
C22—H22 | 0.9300 | C47—H47 | 0.9300 |
C23—C24 | 1.355 (5) | C48—C49 | 1.358 (5) |
C23—H23 | 0.9300 | C48—H48 | 0.9300 |
C24—C25 | 1.399 (5) | C49—C50 | 1.386 (5) |
C24—H24 | 0.9300 | C49—H49 | 0.9300 |
C25—H25 | 0.9300 | C50—H50 | 0.9300 |
C9—N1—C6 | 132.7 (3) | C34—N4—C32 | 132.1 (3) |
C9—N1—H1 | 113.7 | C34—N4—H4A | 114.1 |
C6—N1—H1 | 113.6 | C32—N4—H4A | 113.8 |
C17—N2—N3 | 111.3 (3) | C43—N5—N6 | 111.9 (3) |
C17—N2—C20 | 129.6 (3) | C43—N5—C45 | 129.1 (3) |
N3—N2—C20 | 119.1 (3) | N6—N5—C45 | 118.9 (3) |
C18—N3—N2 | 106.9 (3) | C42—N6—N5 | 106.6 (3) |
C2—C1—H1A | 109.5 | C27—C26—H26A | 109.5 |
C2—C1—H1B | 109.5 | C27—C26—H26B | 109.5 |
H1A—C1—H1B | 109.5 | H26A—C26—H26B | 109.5 |
C2—C1—H1C | 109.5 | C27—C26—H26C | 109.5 |
H1A—C1—H1C | 109.5 | H26A—C26—H26C | 109.5 |
H1B—C1—H1C | 109.5 | H26B—C26—H26C | 109.5 |
C7—C2—C3 | 117.5 (4) | C28—C27—C32 | 116.6 (4) |
C7—C2—C1 | 121.4 (4) | C28—C27—C26 | 120.8 (4) |
C3—C2—C1 | 121.2 (4) | C32—C27—C26 | 122.6 (4) |
C2—C3—C4 | 121.0 (3) | C29—C28—C27 | 122.7 (4) |
C2—C3—H3 | 119.5 | C29—C28—H28 | 118.7 |
C4—C3—H3 | 119.5 | C27—C28—H28 | 118.7 |
C5—C4—C3 | 121.4 (4) | C28—C29—C30 | 120.1 (4) |
C5—C4—H4 | 119.3 | C28—C29—H29 | 120.0 |
C3—C4—H4 | 119.3 | C30—C29—H29 | 120.0 |
C4—C5—C6 | 117.8 (4) | C29—C30—C31 | 118.0 (4) |
C4—C5—C8 | 120.7 (3) | C29—C30—C33 | 121.1 (4) |
C6—C5—C8 | 121.5 (3) | C31—C30—C33 | 120.9 (4) |
C7—C6—C5 | 120.2 (3) | C32—C31—C30 | 121.7 (4) |
C7—C6—N1 | 123.0 (3) | C32—C31—H31 | 119.2 |
C5—C6—N1 | 116.7 (3) | C30—C31—H31 | 119.2 |
C2—C7—C6 | 122.0 (3) | C31—C32—C27 | 120.9 (3) |
C2—C7—H7 | 119.0 | C31—C32—N4 | 122.2 (3) |
C6—C7—H7 | 119.0 | C27—C32—N4 | 116.8 (3) |
C5—C8—H8A | 109.5 | C30—C33—H33A | 109.5 |
C5—C8—H8B | 109.5 | C30—C33—H33B | 109.5 |
H8A—C8—H8B | 109.5 | H33A—C33—H33B | 109.5 |
C5—C8—H8C | 109.5 | C30—C33—H33C | 109.5 |
H8A—C8—H8C | 109.5 | H33A—C33—H33C | 109.5 |
H8B—C8—H8C | 109.5 | H33B—C33—H33C | 109.5 |
N1—C9—C16 | 117.4 (3) | N4—C34—C41 | 118.2 (3) |
N1—C9—C10 | 120.3 (3) | N4—C34—C35 | 119.4 (3) |
C16—C9—C10 | 122.4 (3) | C41—C34—C35 | 122.5 (3) |
C11—C10—C15 | 119.5 (3) | C40—C35—C36 | 118.9 (3) |
C11—C10—C9 | 118.3 (3) | C40—C35—C34 | 118.9 (3) |
C15—C10—C9 | 122.2 (3) | C36—C35—C34 | 122.2 (3) |
C12—C11—C10 | 119.7 (3) | C37—C36—C35 | 120.5 (3) |
C12—C11—H11 | 120.1 | C37—C36—H36 | 119.8 |
C10—C11—H11 | 120.1 | C35—C36—H36 | 119.8 |
C13—C12—C11 | 120.3 (4) | C36—C37—C38 | 119.6 (4) |
C13—C12—H12 | 119.9 | C36—C37—H37 | 120.2 |
C11—C12—H12 | 119.9 | C38—C37—H37 | 120.2 |
C14—C13—C12 | 120.4 (4) | C39—C38—C37 | 120.3 (4) |
C14—C13—H13 | 119.8 | C39—C38—H38 | 119.8 |
C12—C13—H13 | 119.8 | C37—C38—H38 | 119.8 |
C13—C14—C15 | 120.2 (4) | C38—C39—C40 | 120.3 (4) |
C13—C14—H14 | 119.9 | C38—C39—H39 | 119.8 |
C15—C14—H14 | 119.9 | C40—C39—H39 | 119.8 |
C14—C15—C10 | 119.8 (4) | C39—C40—C35 | 120.4 (3) |
C14—C15—H15 | 120.1 | C39—C40—H40 | 119.8 |
C10—C15—H15 | 120.1 | C35—C40—H40 | 119.8 |
C9—C16—C17 | 123.1 (3) | C34—C41—C42 | 132.0 (3) |
C9—C16—C18 | 132.0 (3) | C34—C41—C43 | 122.4 (3) |
C17—C16—C18 | 104.9 (3) | C42—C41—C43 | 105.6 (3) |
O1—C17—N2 | 125.6 (3) | N6—C42—C41 | 111.0 (3) |
O1—C17—C16 | 128.6 (3) | N6—C42—C44 | 119.0 (3) |
N2—C17—C16 | 105.8 (3) | C41—C42—C44 | 129.9 (3) |
N3—C18—C16 | 111.1 (3) | O2—C43—N5 | 126.8 (3) |
N3—C18—C19 | 119.2 (3) | O2—C43—C41 | 128.3 (3) |
C16—C18—C19 | 129.6 (3) | N5—C43—C41 | 104.9 (3) |
C18—C19—H19A | 109.5 | C42—C44—H44A | 109.5 |
C18—C19—H19B | 109.5 | C42—C44—H44B | 109.5 |
H19A—C19—H19B | 109.5 | H44A—C44—H44B | 109.5 |
C18—C19—H19C | 109.5 | C42—C44—H44C | 109.5 |
H19A—C19—H19C | 109.5 | H44A—C44—H44C | 109.5 |
H19B—C19—H19C | 109.5 | H44B—C44—H44C | 109.5 |
C25—C20—C21 | 120.4 (3) | C46—C45—C50 | 119.6 (4) |
C25—C20—N2 | 119.5 (3) | C46—C45—N5 | 121.6 (3) |
C21—C20—N2 | 120.1 (3) | C50—C45—N5 | 118.8 (3) |
C20—C21—C22 | 119.9 (4) | C45—C46—C47 | 120.7 (4) |
C20—C21—H21 | 120.0 | C45—C46—H46 | 119.6 |
C22—C21—H21 | 120.0 | C47—C46—H46 | 119.6 |
C23—C22—C21 | 119.9 (4) | C48—C47—C46 | 119.5 (4) |
C23—C22—H22 | 120.1 | C48—C47—H47 | 120.2 |
C21—C22—H22 | 120.1 | C46—C47—H47 | 120.2 |
C24—C23—C22 | 120.4 (4) | C49—C48—C47 | 120.4 (4) |
C24—C23—H23 | 119.8 | C49—C48—H48 | 119.8 |
C22—C23—H23 | 119.8 | C47—C48—H48 | 119.8 |
C23—C24—C25 | 120.5 (4) | C48—C49—C50 | 120.0 (4) |
C23—C24—H24 | 119.8 | C48—C49—H49 | 120.0 |
C25—C24—H24 | 119.8 | C50—C49—H49 | 120.0 |
C20—C25—C24 | 119.0 (4) | C45—C50—C49 | 119.7 (4) |
C20—C25—H25 | 120.5 | C45—C50—H50 | 120.1 |
C24—C25—H25 | 120.5 | C49—C50—H50 | 120.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.94 | 2.683 (4) | 143 |
N4—H4A···O2 | 0.86 | 1.94 | 2.674 (4) | 142 |
Experimental details
Crystal data | |
Chemical formula | C25H23N3O |
Mr | 381.46 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 24.011 (3), 14.2004 (16), 12.5487 (15) |
β (°) | 104.601 (2) |
V (Å3) | 4140.5 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.982, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26490, 7291, 3103 |
Rint | 0.139 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.144, 0.85 |
No. of reflections | 7291 |
No. of parameters | 530 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.19 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.94 | 2.683 (4) | 143 |
N4—H4A···O2 | 0.86 | 1.94 | 2.674 (4) | 142 |
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The title compound, (I) (Fig. 1) has two methyl substituents in the 2,5-dimethylphenylamino portion of the molecule; the general features are similar to those found in the analogous 2-tolylamino (Bao et al., 2004), 2,4-dimethylphenylamino(Ma et al., 2006b) and 4-tolylamino (Ma, 2005) derivatives. Compound (I) can be used to chelate to a divalent transition metal (Ma et al., 2006a). In both asymmetric molecules of (I), an intramolecular N—H···O hydrogen bond occurs (Table 1).