3-Methyl-4-{[(3-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene)(phen­yl)meth­yl]amino­meth­yl}benz­yl)amino](phen­yl)methyl­idene}-1-phenyl-1H-pyrazol-5(4H)-one

Cai, H.-X.; Wu, W.-N.; Li, X.-X.; Wang, Y.

doi:10.1107/S1600536811027000

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2015

doi:10.1107/S1600536811027000

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3-Methyl-4-{[(3-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(phenyl)methyl]aminomethyl}benzyl)amino](phenyl)methylidene}-1-phenyl-1H-pyrazol-5(4H)-one

Hong-Xin Cai,^a Wei-Na Wu,^a ^* Xiao-Xia Li ^b and Yuan Wang ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China, and ^bInstitute of Functional Materials, Jiangxi University of Finance & Economics, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: wuwn08@hpu.edu.cn

(Received 1 July 2011; accepted 6 July 2011; online 13 July 2011)

The complete molecule of the title compound, C₄₂H₃₆N₆O₂, 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 molecule, one amino group is involved in an intramolecular 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 intermolecular contacts.

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_r = 656.77
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.154
S = 1.01
4290 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	2.04	2.7353 (17)	138

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811027000/vm2108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027000/vm2108Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027000/vm2108Isup3.cml

checkCIF report

Comment top

For our interest in coordination chemistry of the Schiff bases derived from 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) (Wang et al., 2005; Zhang et al., 2010), the crystal structure of the title compound was determined by X-ray diffraction analysis.

As shown in Fig.1, the molecule is generated by a crystallographic two fold axis, with atoms C20 and C22 lying on the axis. In the independent part of the molecule, the two phenyl rings (C1—C6, r.m.s. deviation = 0.0023 Å and C12—C17, r.m.s. deviation = 0.0060 Å) are slightly twisted with respect to the central pyrazolone ring (r.m.s. deviation = 0.0040 Å) making dihedral angles of 6.82 (3)° and 88.32 (6)°, respectively. The non-hydrogen atoms of the phenylenedimethylene group are situated in a fair plane (r.m.s. deviation = 0.0013 Å). The dihedral angles between this plane and the two phenyls in the PMBP moiety are 36.27 (8)° and 82.61 (6)°, respectively. The conformation of the molecule is influenced by an intramolecular hydrogen bond N3—H3A···O1 (Table 1).

Related literature top

For the similar structure of (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 top

A quality of PMBP (1.1 g, 4 mmol) was dissolved in EtOH (50 ml), and an EtOH solution (10 ml) containing (3-(aminomethyl)phenyl)methanamine (0.3 g, 2 mmol) was added dropwise. The mixture was refluxed on a water bath for 3 h, then cooled to room temperature. Yellow block crystals were obtained by slow evaporation of the reaction mixture.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure shown with 30% probability displacement ellipsoids. Unlabelled atoms are related with the labelled ones by symmetry operation -x, y, -z + 1/2.

3-Methyl-4-{[(3-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol- 4-ylidene)(phenyl)methyl]aminomethyl}benzyl)amino](phenyl)methylidene}- 1-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₄₂H₃₆N₆O₂	F(000) = 1384
M_r = 656.77	D_x = 1.214 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5169 reflections
a = 26.4648 (5) Å	θ = 2.5–22.3°
b = 14.3131 (3) Å	µ = 0.08 mm⁻¹
c = 9.5492 (2) Å	T = 296 K
β = 96.766 (1)°	Block, yellow
V = 3591.98 (13) Å³	0.26 × 0.21 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4290 independent reflections
Radiation source: fine-focus sealed tube	2244 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 27.9°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −34→34
T_min = 0.981, T_max = 0.986	k = −18→18
26618 measured reflections	l = −12→12

Refinement top

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.070P)² + 0.8006P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4290 reflections	Δρ_max = 0.14 e Å⁻³
229 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Crystal data top

C₄₂H₃₆N₆O₂	V = 3591.98 (13) Å³
M_r = 656.77	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 26.4648 (5) Å	µ = 0.08 mm⁻¹
b = 14.3131 (3) Å	T = 296 K
c = 9.5492 (2) Å	0.26 × 0.21 × 0.18 mm
β = 96.766 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4290 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2244 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.986	R_int = 0.034
26618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
4290 reflections	Δρ_min = −0.14 e Å⁻³
229 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.10591 (12)	0.05358 (17)	0.2444 (3)	0.1384 (12)
H1	0.1008	−0.0107	0.2429	0.166*
C2	0.06985 (11)	0.11231 (16)	0.1809 (3)	0.1245 (10)
H2	0.0399	0.0873	0.1351	0.149*
C3	0.07646 (8)	0.20769 (14)	0.1825 (3)	0.0910 (7)
H3	0.0513	0.2466	0.1386	0.109*
C4	0.12058 (7)	0.24467 (12)	0.2496 (2)	0.0697 (5)
C5	0.15709 (9)	0.18561 (15)	0.3125 (3)	0.1080 (9)
H5	0.1874	0.2098	0.3576	0.130*
C6	0.14915 (12)	0.09075 (16)	0.3094 (4)	0.1417 (13)
H6	0.1742	0.0514	0.3531	0.170*
C7	0.10172 (6)	0.41413 (11)	0.18660 (19)	0.0584 (4)
C8	0.12958 (6)	0.49712 (11)	0.23182 (18)	0.0561 (4)
C9	0.17273 (6)	0.46540 (13)	0.32301 (18)	0.0625 (5)
C10	0.21466 (8)	0.51993 (14)	0.4038 (2)	0.0895 (7)
H10A	0.2379	0.4778	0.4564	0.134*
H10B	0.2006	0.5618	0.4675	0.134*
H10C	0.2324	0.5552	0.3394	0.134*
C11	0.11435 (6)	0.58586 (11)	0.18703 (18)	0.0551 (4)
C12	0.14287 (6)	0.67116 (11)	0.23827 (18)	0.0569 (4)
C13	0.13372 (8)	0.71405 (13)	0.3608 (2)	0.0756 (5)
H13	0.1088	0.6908	0.4124	0.091*
C14	0.16157 (9)	0.79207 (16)	0.4079 (2)	0.0951 (7)
H14	0.1550	0.8216	0.4906	0.114*
C15	0.19853 (9)	0.82590 (15)	0.3338 (3)	0.0962 (7)
H15	0.2178	0.8773	0.3674	0.115*
C16	0.20722 (9)	0.78489 (16)	0.2119 (3)	0.1021 (8)
H16	0.2319	0.8090	0.1604	0.122*
C17	0.17952 (8)	0.70699 (14)	0.1631 (2)	0.0858 (6)
H17	0.1858	0.6789	0.0790	0.103*
C18	0.05088 (7)	0.68359 (12)	0.0429 (2)	0.0706 (5)
H18A	0.0265	0.6715	−0.0392	0.085*
H18B	0.0773	0.7234	0.0133	0.085*
C19	0.02445 (6)	0.73496 (11)	0.1510 (2)	0.0646 (5)
C20	0.0000	0.68840 (15)	0.2500	0.0621 (7)
H20	0.0000	0.6234	0.2500	0.075*
C21	0.02423 (8)	0.83127 (13)	0.1519 (3)	0.0908 (7)
H21	0.0405	0.8642	0.0861	0.109*
C22	0.0000	0.8787 (2)	0.2500	0.1146 (13)
H22	0.0000	0.9436	0.2500	0.138*
N1	0.12954 (5)	0.34190 (9)	0.25329 (16)	0.0644 (4)
N2	0.17324 (5)	0.37498 (10)	0.33522 (16)	0.0694 (4)
N3	0.07349 (5)	0.59561 (9)	0.09345 (16)	0.0668 (4)
H3A	0.0591	0.5453	0.0597	0.100*
O1	0.06148 (4)	0.40607 (8)	0.10539 (14)	0.0743 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.136 (2)	0.0553 (14)	0.208 (3)	−0.0138 (15)	−0.047 (2)	0.0128 (17)
C2	0.1086 (19)	0.0678 (14)	0.184 (3)	−0.0293 (14)	−0.0386 (19)	0.0169 (16)
C3	0.0764 (13)	0.0606 (12)	0.1302 (19)	−0.0125 (10)	−0.0116 (13)	0.0129 (12)
C4	0.0711 (12)	0.0493 (10)	0.0868 (13)	−0.0025 (9)	0.0016 (10)	−0.0035 (9)
C5	0.0992 (16)	0.0550 (12)	0.156 (2)	0.0067 (11)	−0.0417 (16)	−0.0062 (13)
C6	0.136 (2)	0.0555 (14)	0.215 (3)	0.0057 (14)	−0.062 (2)	0.0043 (16)
C7	0.0522 (9)	0.0513 (10)	0.0712 (11)	−0.0004 (8)	0.0047 (9)	−0.0067 (8)
C8	0.0486 (9)	0.0505 (9)	0.0688 (11)	−0.0022 (7)	0.0048 (8)	−0.0063 (8)
C9	0.0545 (10)	0.0552 (10)	0.0758 (12)	−0.0009 (8)	−0.0003 (9)	−0.0053 (9)
C10	0.0726 (12)	0.0717 (13)	0.1153 (17)	−0.0063 (10)	−0.0257 (12)	−0.0031 (12)
C11	0.0451 (8)	0.0531 (10)	0.0672 (11)	−0.0003 (7)	0.0075 (8)	−0.0058 (8)
C12	0.0517 (9)	0.0484 (9)	0.0690 (11)	−0.0031 (7)	0.0004 (8)	−0.0032 (8)
C13	0.0790 (12)	0.0730 (13)	0.0753 (13)	−0.0160 (10)	0.0109 (10)	−0.0137 (10)
C14	0.1101 (18)	0.0861 (15)	0.0869 (15)	−0.0199 (14)	0.0023 (14)	−0.0292 (12)
C15	0.0974 (16)	0.0703 (14)	0.1161 (19)	−0.0291 (12)	−0.0069 (15)	−0.0165 (14)
C16	0.0932 (16)	0.0910 (16)	0.124 (2)	−0.0426 (13)	0.0228 (15)	−0.0114 (15)
C17	0.0831 (13)	0.0806 (14)	0.0974 (15)	−0.0274 (11)	0.0265 (12)	−0.0194 (12)
C18	0.0580 (10)	0.0597 (11)	0.0907 (14)	−0.0013 (8)	−0.0054 (10)	0.0099 (10)
C19	0.0492 (9)	0.0456 (9)	0.0944 (14)	−0.0025 (7)	−0.0106 (9)	0.0049 (9)
C20	0.0508 (13)	0.0358 (11)	0.0960 (19)	0.000	−0.0072 (13)	0.000
C21	0.0942 (15)	0.0489 (11)	0.130 (2)	−0.0071 (10)	0.0134 (14)	0.0107 (11)
C22	0.131 (3)	0.0378 (14)	0.179 (4)	0.000	0.037 (3)	0.000
N1	0.0574 (8)	0.0501 (8)	0.0826 (10)	−0.0003 (7)	−0.0051 (8)	−0.0051 (7)
N2	0.0603 (9)	0.0580 (9)	0.0862 (11)	0.0006 (7)	−0.0066 (8)	−0.0040 (8)
N3	0.0537 (8)	0.0528 (8)	0.0905 (11)	−0.0027 (6)	−0.0050 (8)	−0.0051 (7)
O1	0.0579 (7)	0.0572 (7)	0.1023 (10)	−0.0039 (6)	−0.0132 (7)	−0.0077 (6)

Geometric parameters (Å, º) top

C1—C6	1.346 (4)	C12—C17	1.372 (2)
C1—C2	1.359 (3)	C13—C14	1.384 (3)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.376 (3)	C14—C15	1.362 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.370 (3)	C15—C16	1.347 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.369 (3)	C16—C17	1.385 (3)
C4—N1	1.412 (2)	C16—H16	0.9300
C5—C6	1.374 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—N3	1.452 (2)
C6—H6	0.9300	C18—C19	1.506 (3)
C7—O1	1.2465 (19)	C18—H18A	0.9700
C7—N1	1.381 (2)	C18—H18B	0.9700
C7—C8	1.437 (2)	C19—C20	1.378 (2)
C8—C11	1.385 (2)	C19—C21	1.379 (2)
C8—C9	1.426 (2)	C20—C19ⁱ	1.378 (2)
C9—N2	1.299 (2)	C20—H20	0.9300
C9—C10	1.495 (2)	C21—C22	1.375 (2)
C10—H10A	0.9600	C21—H21	0.9300
C10—H10B	0.9600	C22—C21ⁱ	1.375 (2)
C10—H10C	0.9600	C22—H22	0.9300
C11—N3	1.327 (2)	N1—N2	1.4002 (19)
C11—C12	1.488 (2)	N3—H3A	0.8600
C12—C13	1.368 (2)

C6—C1—C2	118.4 (2)	C12—C13—H13	120.0
C6—C1—H1	120.8	C14—C13—H13	120.0
C2—C1—H1	120.8	C15—C14—C13	120.4 (2)
C1—C2—C3	121.8 (2)	C15—C14—H14	119.8
C1—C2—H2	119.1	C13—C14—H14	119.8
C3—C2—H2	119.1	C16—C15—C14	120.0 (2)
C4—C3—C2	119.2 (2)	C16—C15—H15	120.0
C4—C3—H3	120.4	C14—C15—H15	120.0
C2—C3—H3	120.4	C15—C16—C17	120.3 (2)
C5—C4—C3	119.04 (18)	C15—C16—H16	119.9
C5—C4—N1	119.34 (17)	C17—C16—H16	119.9
C3—C4—N1	121.61 (17)	C12—C17—C16	120.2 (2)
C4—C5—C6	120.2 (2)	C12—C17—H17	119.9
C4—C5—H5	119.9	C16—C17—H17	119.9
C6—C5—H5	119.9	N3—C18—C19	113.69 (15)
C1—C6—C5	121.4 (2)	N3—C18—H18A	108.8
C1—C6—H6	119.3	C19—C18—H18A	108.8
C5—C6—H6	119.3	N3—C18—H18B	108.8
O1—C7—N1	126.00 (15)	C19—C18—H18B	108.8
O1—C7—C8	129.32 (15)	H18A—C18—H18B	107.7
N1—C7—C8	104.68 (14)	C20—C19—C21	118.47 (19)
C11—C8—C9	131.56 (15)	C20—C19—C18	121.86 (15)
C11—C8—C7	123.01 (15)	C21—C19—C18	119.68 (18)
C9—C8—C7	105.42 (14)	C19—C20—C19ⁱ	122.2 (2)
N2—C9—C8	111.78 (15)	C19—C20—H20	118.9
N2—C9—C10	118.33 (16)	C19ⁱ—C20—H20	118.9
C8—C9—C10	129.89 (16)	C22—C21—C19	120.0 (2)
C9—C10—H10A	109.5	C22—C21—H21	120.0
C9—C10—H10B	109.5	C19—C21—H21	120.0
H10A—C10—H10B	109.5	C21ⁱ—C22—C21	120.9 (3)
C9—C10—H10C	109.5	C21ⁱ—C22—H22	119.6
H10A—C10—H10C	109.5	C21—C22—H22	119.6
H10B—C10—H10C	109.5	C7—N1—N2	111.41 (13)
N3—C11—C8	119.28 (14)	C7—N1—C4	130.37 (15)
N3—C11—C12	118.49 (14)	N2—N1—C4	118.22 (14)
C8—C11—C12	122.23 (15)	C9—N2—N1	106.70 (14)
C13—C12—C17	119.14 (16)	C11—N3—C18	125.91 (14)
C13—C12—C11	121.05 (15)	C11—N3—H3A	117.0
C17—C12—C11	119.81 (16)	C18—N3—H3A	117.0
C12—C13—C14	119.96 (19)

C6—C1—C2—C3	−0.4 (5)	C13—C14—C15—C16	1.8 (4)
C1—C2—C3—C4	0.1 (5)	C14—C15—C16—C17	−1.5 (4)
C2—C3—C4—C5	0.4 (4)	C13—C12—C17—C16	0.8 (3)
C2—C3—C4—N1	179.4 (2)	C11—C12—C17—C16	−178.25 (19)
C3—C4—C5—C6	−0.7 (4)	C15—C16—C17—C12	0.2 (4)
N1—C4—C5—C6	−179.7 (3)	N3—C18—C19—C20	−33.2 (2)
C2—C1—C6—C5	0.1 (6)	N3—C18—C19—C21	147.11 (18)
C4—C5—C6—C1	0.4 (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—C11	179.42 (15)	C20—C19—C21—C22	0.0 (3)
O1—C7—C8—C9	−179.44 (17)	C18—C19—C21—C22	179.75 (15)
N1—C7—C8—C9	0.36 (18)	C19—C21—C22—C21ⁱ	−0.01 (13)
C11—C8—C9—N2	−178.64 (17)	O1—C7—N1—N2	178.94 (16)
C7—C8—C9—N2	0.3 (2)	C8—C7—N1—N2	−0.88 (18)
C11—C8—C9—C10	2.4 (3)	O1—C7—N1—C4	−0.6 (3)
C7—C8—C9—C10	−178.61 (19)	C8—C7—N1—C4	179.55 (18)
C9—C8—C11—N3	175.76 (17)	C5—C4—N1—C7	172.5 (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—C12	178.17 (15)	C3—C4—N1—N2	173.93 (18)
N3—C11—C12—C13	95.4 (2)	C8—C9—N2—N1	−0.8 (2)
C8—C11—C12—C13	−85.8 (2)	C10—C9—N2—N1	178.22 (16)
N3—C11—C12—C17	−85.6 (2)	C7—N1—N2—C9	1.09 (19)
C8—C11—C12—C17	93.2 (2)	C4—N1—N2—C9	−179.28 (16)
C17—C12—C13—C14	−0.5 (3)	C8—C11—N3—C18	175.89 (16)
C11—C12—C13—C14	178.51 (18)	C12—C11—N3—C18	−5.2 (3)
C12—C13—C14—C15	−0.8 (3)	C19—C18—N3—C11	−71.2 (2)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.04	2.7353 (17)	138

Experimental details

Crystal data
Chemical formula	C₄₂H₃₆N₆O₂
M_r	656.77
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	26.4648 (5), 14.3131 (3), 9.5492 (2)
β (°)	96.766 (1)
V (Å³)	3591.98 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.21 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.981, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	26618, 4290, 2244
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.154, 1.01
No. of reflections	4290
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.04	2.7353 (17)	138

Acknowledgements

The authors are grateful to the Natural Science Foundation of Jiangxi Province for financial support (No. 2010GQS0064).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA . Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y. & Yang, Z.-Y. (2005). Transition Met. Chem. 30, 902–906. Web of Science CrossRef CAS Google Scholar
Zhang, Z.-P., Wang, Y., Li, X.-X. & Li, Y.-W. (2010). Acta Cryst. E66, o3326. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o2015

doi:10.1107/S1600536811027000

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Methyl-4-{[(3-{[(3-methyl-5-oxo-1-phenyl-4,5-di­hydro-1H-pyrazol-4-yl­­idene)(phen­yl)meth­yl]amino­meth­yl}benz­yl)amino](phen­yl)methyl­­idene}-1-phenyl-1H-pyrazol-5(4H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Methyl-4-{[(3-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(phenyl)methyl]aminomethyl}benzyl)amino](phenyl)methylidene}-1-phenyl-1H-pyrazol-5(4H)-one