Literature DB >> 22091047

3-Methyl-4-{[(3-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl-idene)(phen-yl)meth-yl]amino-meth-yl}benz-yl)amino](phen-yl)methyl-idene}-1-phenyl-1H-pyrazol-5(4H)-one.

Hong-Xin Cai, Wei-Na Wu, Xiao-Xia Li, Yuan Wang.   

Abstract

The complete mol-ecule of the title compound, C(42)H(36)N(6)O(2), is generated by a crystallographic twofold axis with two C atoms of the central phenyl group lying on the axis. In the independent part of the mol-ecule, one amino group is involved in an intra-molecular N-H⋯O hydrogen bond, and the two adjacent phenyl rings are twisted from the plane of the pyrazolone ring with dihedral angles of 6.82 (3) and 88.32 (6)°. The crystal packing exhibits no classical inter-molecular contacts.

Entities:  

Year:  2011        PMID： 22091047      PMCID： PMC3213468          DOI： 10.1107/S1600536811027000

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the similar structure (E,E)-3,3′-dimethyl-1,1′-diphenyl-4,4′-{(3-aza­pentane-1,5-diyldiimino)­bis­[phenyl­methyl­idyne]}di-1H-pyrazol-5(4H)-one, see: Zhang et al. (2010 ▶). For the DNA binding properties of transition metal complexes with the above Schiff base, see: Wang & Yang (2005 ▶).

Experimental

Crystal data

C42H36N6O2 M = 656.77 Monoclinic, a = 26.4648 (5) Å b = 14.3131 (3) Å c = 9.5492 (2) Å β = 96.766 (1)° V = 3591.98 (13) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 296 K 0.26 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.981, T max = 0.986 26618 measured reflections 4290 independent reflections 2244 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.154 S = 1.01 4290 reflections 229 parameters H-atom parameters constrained Δρmax = 0.14 e Å−3 Δρmin = −0.14 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027000/vm2108sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027000/vm2108Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811027000/vm2108Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C42H36N6O2F(000) = 1384
Mr = 656.77Dx = 1.214 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5169 reflections
a = 26.4648 (5) Åθ = 2.5–22.3°
b = 14.3131 (3) ŵ = 0.08 mm−1
c = 9.5492 (2) ÅT = 296 K
β = 96.766 (1)°Block, yellow
V = 3591.98 (13) Å30.26 × 0.21 × 0.18 mm
Z = 4
Bruker APEXII CCD diffractometer4290 independent reflections
Radiation source: fine-focus sealed tube2244 reflections with I > 2σ(I)
graphiteRint = 0.034
φ and ω scansθmax = 27.9°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −34→34
Tmin = 0.981, Tmax = 0.986k = −18→18
26618 measured reflectionsl = −12→12
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.154w = 1/[σ2(Fo2) + (0.070P)2 + 0.8006P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4290 reflectionsΔρmax = 0.14 e Å−3
229 parametersΔρmin = −0.14 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0014 (3)
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.
xyzUiso*/Ueq
C10.10591 (12)0.05358 (17)0.2444 (3)0.1384 (12)
H10.1008−0.01070.24290.166*
C20.06985 (11)0.11231 (16)0.1809 (3)0.1245 (10)
H20.03990.08730.13510.149*
C30.07646 (8)0.20769 (14)0.1825 (3)0.0910 (7)
H30.05130.24660.13860.109*
C40.12058 (7)0.24467 (12)0.2496 (2)0.0697 (5)
C50.15709 (9)0.18561 (15)0.3125 (3)0.1080 (9)
H50.18740.20980.35760.130*
C60.14915 (12)0.09075 (16)0.3094 (4)0.1417 (13)
H60.17420.05140.35310.170*
C70.10172 (6)0.41413 (11)0.18660 (19)0.0584 (4)
C80.12958 (6)0.49712 (11)0.23182 (18)0.0561 (4)
C90.17273 (6)0.46540 (13)0.32301 (18)0.0625 (5)
C100.21466 (8)0.51993 (14)0.4038 (2)0.0895 (7)
H10A0.23790.47780.45640.134*
H10B0.20060.56180.46750.134*
H10C0.23240.55520.33940.134*
C110.11435 (6)0.58586 (11)0.18703 (18)0.0551 (4)
C120.14287 (6)0.67116 (11)0.23827 (18)0.0569 (4)
C130.13372 (8)0.71405 (13)0.3608 (2)0.0756 (5)
H130.10880.69080.41240.091*
C140.16157 (9)0.79207 (16)0.4079 (2)0.0951 (7)
H140.15500.82160.49060.114*
C150.19853 (9)0.82590 (15)0.3338 (3)0.0962 (7)
H150.21780.87730.36740.115*
C160.20722 (9)0.78489 (16)0.2119 (3)0.1021 (8)
H160.23190.80900.16040.122*
C170.17952 (8)0.70699 (14)0.1631 (2)0.0858 (6)
H170.18580.67890.07900.103*
C180.05088 (7)0.68359 (12)0.0429 (2)0.0706 (5)
H18A0.02650.6715−0.03920.085*
H18B0.07730.72340.01330.085*
C190.02445 (6)0.73496 (11)0.1510 (2)0.0646 (5)
C200.00000.68840 (15)0.25000.0621 (7)
H200.00000.62340.25000.075*
C210.02423 (8)0.83127 (13)0.1519 (3)0.0908 (7)
H210.04050.86420.08610.109*
C220.00000.8787 (2)0.25000.1146 (13)
H220.00000.94360.25000.138*
N10.12954 (5)0.34190 (9)0.25329 (16)0.0644 (4)
N20.17324 (5)0.37498 (10)0.33522 (16)0.0694 (4)
N30.07349 (5)0.59561 (9)0.09345 (16)0.0668 (4)
H3A0.05910.54530.05970.100*
O10.06148 (4)0.40607 (8)0.10539 (14)0.0743 (4)
U11U22U33U12U13U23
C10.136 (2)0.0553 (14)0.208 (3)−0.0138 (15)−0.047 (2)0.0128 (17)
C20.1086 (19)0.0678 (14)0.184 (3)−0.0293 (14)−0.0386 (19)0.0169 (16)
C30.0764 (13)0.0606 (12)0.1302 (19)−0.0125 (10)−0.0116 (13)0.0129 (12)
C40.0711 (12)0.0493 (10)0.0868 (13)−0.0025 (9)0.0016 (10)−0.0035 (9)
C50.0992 (16)0.0550 (12)0.156 (2)0.0067 (11)−0.0417 (16)−0.0062 (13)
C60.136 (2)0.0555 (14)0.215 (3)0.0057 (14)−0.062 (2)0.0043 (16)
C70.0522 (9)0.0513 (10)0.0712 (11)−0.0004 (8)0.0047 (9)−0.0067 (8)
C80.0486 (9)0.0505 (9)0.0688 (11)−0.0022 (7)0.0048 (8)−0.0063 (8)
C90.0545 (10)0.0552 (10)0.0758 (12)−0.0009 (8)−0.0003 (9)−0.0053 (9)
C100.0726 (12)0.0717 (13)0.1153 (17)−0.0063 (10)−0.0257 (12)−0.0031 (12)
C110.0451 (8)0.0531 (10)0.0672 (11)−0.0003 (7)0.0075 (8)−0.0058 (8)
C120.0517 (9)0.0484 (9)0.0690 (11)−0.0031 (7)0.0004 (8)−0.0032 (8)
C130.0790 (12)0.0730 (13)0.0753 (13)−0.0160 (10)0.0109 (10)−0.0137 (10)
C140.1101 (18)0.0861 (15)0.0869 (15)−0.0199 (14)0.0023 (14)−0.0292 (12)
C150.0974 (16)0.0703 (14)0.1161 (19)−0.0291 (12)−0.0069 (15)−0.0165 (14)
C160.0932 (16)0.0910 (16)0.124 (2)−0.0426 (13)0.0228 (15)−0.0114 (15)
C170.0831 (13)0.0806 (14)0.0974 (15)−0.0274 (11)0.0265 (12)−0.0194 (12)
C180.0580 (10)0.0597 (11)0.0907 (14)−0.0013 (8)−0.0054 (10)0.0099 (10)
C190.0492 (9)0.0456 (9)0.0944 (14)−0.0025 (7)−0.0106 (9)0.0049 (9)
C200.0508 (13)0.0358 (11)0.0960 (19)0.000−0.0072 (13)0.000
C210.0942 (15)0.0489 (11)0.130 (2)−0.0071 (10)0.0134 (14)0.0107 (11)
C220.131 (3)0.0378 (14)0.179 (4)0.0000.037 (3)0.000
N10.0574 (8)0.0501 (8)0.0826 (10)−0.0003 (7)−0.0051 (8)−0.0051 (7)
N20.0603 (9)0.0580 (9)0.0862 (11)0.0006 (7)−0.0066 (8)−0.0040 (8)
N30.0537 (8)0.0528 (8)0.0905 (11)−0.0027 (6)−0.0050 (8)−0.0051 (7)
O10.0579 (7)0.0572 (7)0.1023 (10)−0.0039 (6)−0.0132 (7)−0.0077 (6)
C1—C61.346 (4)C12—C171.372 (2)
C1—C21.359 (3)C13—C141.384 (3)
C1—H10.9300C13—H130.9300
C2—C31.376 (3)C14—C151.362 (3)
C2—H20.9300C14—H140.9300
C3—C41.370 (3)C15—C161.347 (3)
C3—H30.9300C15—H150.9300
C4—C51.369 (3)C16—C171.385 (3)
C4—N11.412 (2)C16—H160.9300
C5—C61.374 (3)C17—H170.9300
C5—H50.9300C18—N31.452 (2)
C6—H60.9300C18—C191.506 (3)
C7—O11.2465 (19)C18—H18A0.9700
C7—N11.381 (2)C18—H18B0.9700
C7—C81.437 (2)C19—C201.378 (2)
C8—C111.385 (2)C19—C211.379 (2)
C8—C91.426 (2)C20—C19i1.378 (2)
C9—N21.299 (2)C20—H200.9300
C9—C101.495 (2)C21—C221.375 (2)
C10—H10A0.9600C21—H210.9300
C10—H10B0.9600C22—C21i1.375 (2)
C10—H10C0.9600C22—H220.9300
C11—N31.327 (2)N1—N21.4002 (19)
C11—C121.488 (2)N3—H3A0.8600
C12—C131.368 (2)
C6—C1—C2118.4 (2)C12—C13—H13120.0
C6—C1—H1120.8C14—C13—H13120.0
C2—C1—H1120.8C15—C14—C13120.4 (2)
C1—C2—C3121.8 (2)C15—C14—H14119.8
C1—C2—H2119.1C13—C14—H14119.8
C3—C2—H2119.1C16—C15—C14120.0 (2)
C4—C3—C2119.2 (2)C16—C15—H15120.0
C4—C3—H3120.4C14—C15—H15120.0
C2—C3—H3120.4C15—C16—C17120.3 (2)
C5—C4—C3119.04 (18)C15—C16—H16119.9
C5—C4—N1119.34 (17)C17—C16—H16119.9
C3—C4—N1121.61 (17)C12—C17—C16120.2 (2)
C4—C5—C6120.2 (2)C12—C17—H17119.9
C4—C5—H5119.9C16—C17—H17119.9
C6—C5—H5119.9N3—C18—C19113.69 (15)
C1—C6—C5121.4 (2)N3—C18—H18A108.8
C1—C6—H6119.3C19—C18—H18A108.8
C5—C6—H6119.3N3—C18—H18B108.8
O1—C7—N1126.00 (15)C19—C18—H18B108.8
O1—C7—C8129.32 (15)H18A—C18—H18B107.7
N1—C7—C8104.68 (14)C20—C19—C21118.47 (19)
C11—C8—C9131.56 (15)C20—C19—C18121.86 (15)
C11—C8—C7123.01 (15)C21—C19—C18119.68 (18)
C9—C8—C7105.42 (14)C19—C20—C19i122.2 (2)
N2—C9—C8111.78 (15)C19—C20—H20118.9
N2—C9—C10118.33 (16)C19i—C20—H20118.9
C8—C9—C10129.89 (16)C22—C21—C19120.0 (2)
C9—C10—H10A109.5C22—C21—H21120.0
C9—C10—H10B109.5C19—C21—H21120.0
H10A—C10—H10B109.5C21i—C22—C21120.9 (3)
C9—C10—H10C109.5C21i—C22—H22119.6
H10A—C10—H10C109.5C21—C22—H22119.6
H10B—C10—H10C109.5C7—N1—N2111.41 (13)
N3—C11—C8119.28 (14)C7—N1—C4130.37 (15)
N3—C11—C12118.49 (14)N2—N1—C4118.22 (14)
C8—C11—C12122.23 (15)C9—N2—N1106.70 (14)
C13—C12—C17119.14 (16)C11—N3—C18125.91 (14)
C13—C12—C11121.05 (15)C11—N3—H3A117.0
C17—C12—C11119.81 (16)C18—N3—H3A117.0
C12—C13—C14119.96 (19)
C6—C1—C2—C3−0.4 (5)C13—C14—C15—C161.8 (4)
C1—C2—C3—C40.1 (5)C14—C15—C16—C17−1.5 (4)
C2—C3—C4—C50.4 (4)C13—C12—C17—C160.8 (3)
C2—C3—C4—N1179.4 (2)C11—C12—C17—C16−178.25 (19)
C3—C4—C5—C6−0.7 (4)C15—C16—C17—C120.2 (4)
N1—C4—C5—C6−179.7 (3)N3—C18—C19—C20−33.2 (2)
C2—C1—C6—C50.1 (6)N3—C18—C19—C21147.11 (18)
C4—C5—C6—C10.4 (5)C21—C19—C20—C19i−0.01 (13)
O1—C7—C8—C11−0.4 (3)C18—C19—C20—C19i−179.73 (17)
N1—C7—C8—C11179.42 (15)C20—C19—C21—C220.0 (3)
O1—C7—C8—C9−179.44 (17)C18—C19—C21—C22179.75 (15)
N1—C7—C8—C90.36 (18)C19—C21—C22—C21i−0.01 (13)
C11—C8—C9—N2−178.64 (17)O1—C7—N1—N2178.94 (16)
C7—C8—C9—N20.3 (2)C8—C7—N1—N2−0.88 (18)
C11—C8—C9—C102.4 (3)O1—C7—N1—C4−0.6 (3)
C7—C8—C9—C10−178.61 (19)C8—C7—N1—C4179.55 (18)
C9—C8—C11—N3175.76 (17)C5—C4—N1—C7172.5 (2)
C7—C8—C11—N3−3.0 (3)C3—C4—N1—C7−6.5 (3)
C9—C8—C11—C12−3.1 (3)C5—C4—N1—N2−7.1 (3)
C7—C8—C11—C12178.17 (15)C3—C4—N1—N2173.93 (18)
N3—C11—C12—C1395.4 (2)C8—C9—N2—N1−0.8 (2)
C8—C11—C12—C13−85.8 (2)C10—C9—N2—N1178.22 (16)
N3—C11—C12—C17−85.6 (2)C7—N1—N2—C91.09 (19)
C8—C11—C12—C1793.2 (2)C4—N1—N2—C9−179.28 (16)
C17—C12—C13—C14−0.5 (3)C8—C11—N3—C18175.89 (16)
C11—C12—C13—C14178.51 (18)C12—C11—N3—C18−5.2 (3)
C12—C13—C14—C15−0.8 (3)C19—C18—N3—C11−71.2 (2)
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.862.042.7353 (17)138
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N3—H3A⋯O10.862.042.7353 (17)138
  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  (E,E)-3,3'-Dimethyl-1,1'-diphenyl-4,4'-{[3-aza-pentane-1,5-diylbis(aza-nedi-yl)]bis-(phenyl-methyl-idyne)}di-1H-pyrazol-5(4H)-one.

Authors:  Zhao-Po Zhang; Yuan Wang; Xiao-Xia Li; Yan-Wei Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-27
  2 in total

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