(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.

The asymmetric unit of the title compound, C(38)H(37)N(7)O(2), contains one half-mol-ecule, situated on a twofold rotational axis, in which one amino group is involved in intra-molecular N-H⋯O hydrogen bond and the two phenyl rings are twisted from the plane of pyrazolone ring by 26.69 (10) and 79.64 (8)°. The crystal packing exhibits no classical inter-molecular contacts.

Related literature

For the synthesis of the title compound and the DNA binding properties of its transition metal complexes, see: Yang et al. (2000 ▶); Wang & Yang (2005 ▶). For the similar structure of (E,E)-3,3′-dimethyl-1,1′-diphenyl-4,4′-{(ethane-1,2-diyldiimino)­bis­[(2-fur­yl)-methyl­idyne]}di-1H-pyrazol-5(4H)-one, see: Wang (2010 ▶).

Experimental

Crystal data

C38H37N7O2

M = 623.75

Monoclinic,

a = 20.3219 (8) Å

b = 8.1990 (2) Å

c = 20.5468 (6) Å

β = 106.748 (2)°

V = 3278.27 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.23 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.982, T max = 0.988

8269 measured reflections

3765 independent reflections

1886 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.179

S = 1.01

3765 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.29 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 datablocks I, global. DOI: 10.1107/S1600536810048981/cv5005sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048981/cv5005Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C38H37N7O2	F(000) = 1320
Mr = 623.75	Dx = 1.264 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.3219 (8) Å	Cell parameters from 1721 reflections
b = 8.1990 (2) Å	θ = 2.5–22.0°
c = 20.5468 (6) Å	µ = 0.08 mm−1
β = 106.748 (2)°	T = 296 K
V = 3278.27 (18) Å3	Block, yellow
Z = 4	0.23 × 0.21 × 0.15 mm

Bruker SMART APEXII CCD diffractometer	3765 independent reflections
Radiation source: fine-focus sealed tube	1886 reflections with I > 2σ(I)
graphite	Rint = 0.021
phi and ω scans	θmax = 27.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −26→20
Tmin = 0.982, Tmax = 0.988	k = −8→10
8269 measured reflections	l = −26→25

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) = 0.179	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0884P)2 + 0.1149P] where P = (Fo2 + 2Fc2)/3
3765 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.29 e Å−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.

	x	y	z	Uiso*/Ueq
O1	0.06573 (8)	0.23883 (18)	0.35444 (8)	0.0809 (5)
N1	0.14838 (9)	0.0606 (2)	0.41990 (8)	0.0707 (5)
C7	0.12657 (11)	0.1980 (3)	0.38051 (10)	0.0645 (6)
C12	0.25215 (10)	0.4844 (3)	0.32781 (11)	0.0661 (6)
N2	0.21985 (10)	0.0439 (3)	0.43823 (10)	0.0819 (6)
N3	0.12874 (9)	0.4629 (2)	0.29494 (10)	0.0833 (6)
H3A	0.0927	0.4145	0.2992	0.100*
C11	0.18821 (10)	0.4066 (3)	0.33364 (11)	0.0657 (6)
N4	0.0000	0.6106 (3)	0.2500	0.0898 (9)
H4	0.0000	0.5057	0.2500	0.108*
C8	0.18835 (10)	0.2749 (3)	0.37639 (10)	0.0635 (6)
C6	0.10856 (13)	−0.0732 (3)	0.42954 (10)	0.0719 (6)
C17	0.27276 (12)	0.4657 (3)	0.27000 (11)	0.0738 (6)
H17	0.2456	0.4070	0.2333	0.089*
C9	0.24330 (11)	0.1713 (3)	0.41344 (10)	0.0715 (6)
C19	0.06028 (11)	0.7026 (3)	0.25289 (12)	0.0802 (7)
H19A	0.0749	0.7608	0.2958	0.096*
H19B	0.0500	0.7825	0.2165	0.096*
C15	0.37336 (13)	0.6229 (3)	0.32006 (17)	0.0930 (8)
H15	0.4144	0.6685	0.3174	0.112*
C13	0.29269 (12)	0.5747 (3)	0.38196 (12)	0.0822 (7)
H13	0.2791	0.5876	0.4212	0.099*
C16	0.33348 (14)	0.5339 (3)	0.26650 (14)	0.0840 (7)
H16	0.3476	0.5196	0.2277	0.101*
C5	0.04144 (14)	−0.0517 (3)	0.42877 (12)	0.0830 (7)
H5	0.0224	0.0524	0.4239	0.100*
C18	0.11649 (12)	0.5955 (3)	0.24635 (13)	0.0913 (8)
H18A	0.1048	0.5511	0.2007	0.110*
H18B	0.1582	0.6592	0.2535	0.110*
C14	0.35261 (13)	0.6447 (3)	0.37766 (15)	0.0951 (8)
H14	0.3792	0.7068	0.4136	0.114*
C10	0.31871 (12)	0.1867 (4)	0.42487 (13)	0.0961 (8)
H10A	0.3412	0.0905	0.4472	0.144*
H10B	0.3354	0.2803	0.4528	0.144*
H10C	0.3281	0.1991	0.3820	0.144*
C1	0.13730 (17)	−0.2275 (3)	0.43868 (12)	0.0930 (8)
H1	0.1832	−0.2428	0.4409	0.112*
C2	0.0968 (2)	−0.3578 (4)	0.44439 (14)	0.1196 (12)
H2	0.1156	−0.4621	0.4496	0.144*
C4	0.00213 (17)	−0.1842 (4)	0.43516 (14)	0.1080 (9)
H4A	−0.0435	−0.1692	0.4344	0.130*
C3	0.0297 (3)	−0.3380 (5)	0.44262 (15)	0.1220 (12)
H3	0.0030	−0.4276	0.4464	0.146*

	U11	U22	U33	U12	U13	U23
O1	0.0582 (10)	0.0849 (11)	0.0935 (11)	0.0105 (8)	0.0123 (8)	0.0203 (9)
N1	0.0691 (12)	0.0775 (12)	0.0639 (11)	0.0186 (10)	0.0165 (9)	0.0105 (10)
C7	0.0633 (14)	0.0714 (13)	0.0550 (11)	0.0118 (11)	0.0113 (10)	0.0031 (11)
C12	0.0527 (12)	0.0789 (14)	0.0630 (13)	0.0104 (10)	0.0106 (10)	0.0064 (11)
N2	0.0710 (13)	0.1030 (15)	0.0698 (12)	0.0299 (11)	0.0171 (9)	0.0151 (11)
N3	0.0534 (11)	0.0994 (14)	0.0904 (14)	0.0020 (10)	0.0098 (9)	0.0312 (12)
C11	0.0534 (12)	0.0782 (14)	0.0613 (12)	0.0071 (11)	0.0099 (9)	−0.0004 (11)
N4	0.0586 (17)	0.0646 (15)	0.141 (3)	0.000	0.0209 (16)	0.000
C8	0.0578 (13)	0.0768 (14)	0.0529 (11)	0.0114 (11)	0.0109 (9)	0.0040 (11)
C6	0.0888 (17)	0.0736 (15)	0.0502 (11)	0.0087 (13)	0.0153 (11)	0.0050 (11)
C17	0.0676 (15)	0.0905 (16)	0.0623 (13)	0.0129 (12)	0.0171 (11)	0.0103 (12)
C9	0.0635 (14)	0.0937 (16)	0.0556 (12)	0.0222 (13)	0.0144 (10)	0.0047 (12)
C19	0.0640 (15)	0.0849 (15)	0.0790 (15)	−0.0046 (13)	0.0001 (11)	0.0105 (13)
C15	0.0587 (15)	0.0976 (19)	0.118 (2)	0.0060 (14)	0.0185 (15)	0.0314 (18)
C13	0.0626 (14)	0.1095 (18)	0.0691 (14)	0.0038 (14)	0.0101 (11)	−0.0065 (14)
C16	0.0793 (18)	0.0950 (17)	0.0848 (17)	0.0241 (14)	0.0348 (14)	0.0294 (15)
C5	0.0876 (18)	0.0819 (16)	0.0771 (15)	−0.0009 (14)	0.0201 (13)	0.0111 (13)
C18	0.0667 (15)	0.1080 (18)	0.0938 (17)	0.0109 (14)	0.0146 (12)	0.0381 (15)
C14	0.0646 (17)	0.110 (2)	0.101 (2)	−0.0025 (14)	0.0075 (14)	−0.0023 (16)
C10	0.0650 (16)	0.134 (2)	0.0863 (16)	0.0318 (15)	0.0163 (12)	0.0204 (16)
C1	0.136 (2)	0.0787 (17)	0.0666 (14)	0.0274 (17)	0.0325 (15)	0.0120 (13)
C2	0.205 (4)	0.074 (2)	0.0774 (19)	0.014 (2)	0.037 (2)	0.0158 (15)
C4	0.119 (2)	0.105 (2)	0.0920 (19)	−0.020 (2)	0.0188 (16)	0.0229 (17)
C3	0.182 (4)	0.100 (3)	0.0778 (18)	−0.037 (3)	0.026 (2)	0.0155 (17)

O1—C7	1.243 (2)	C19—H19A	0.9700
N1—C7	1.383 (3)	C19—H19B	0.9700
N1—N2	1.398 (2)	C15—C16	1.374 (4)
N1—C6	1.411 (3)	C15—C14	1.378 (4)
C7—C8	1.429 (3)	C15—H15	0.9300
C12—C17	1.377 (3)	C13—C14	1.372 (3)
C12—C13	1.391 (3)	C13—H13	0.9300
C12—C11	1.483 (3)	C16—H16	0.9300
N2—C9	1.310 (3)	C5—C4	1.377 (4)
N3—C11	1.324 (3)	C5—H5	0.9300
N3—C18	1.448 (3)	C18—H18A	0.9700
N3—H3A	0.8600	C18—H18B	0.9700
C11—C8	1.392 (3)	C14—H14	0.9300
N4—C19	1.425 (3)	C10—H10A	0.9600
N4—C19i	1.425 (3)	C10—H10B	0.9600
N4—H4	0.8600	C10—H10C	0.9600
C8—C9	1.435 (3)	C1—C2	1.375 (4)
C6—C5	1.371 (3)	C1—H1	0.9300
C6—C1	1.384 (3)	C2—C3	1.362 (5)
C17—C16	1.375 (3)	C2—H2	0.9300
C17—H17	0.9300	C4—C3	1.370 (5)
C9—C10	1.487 (3)	C4—H4A	0.9300
C19—C18	1.477 (3)	C3—H3	0.9300
C7—N1—N2	111.73 (18)	C16—C15—H15	120.0
C7—N1—C6	127.98 (19)	C14—C15—H15	120.0
N2—N1—C6	118.64 (18)	C14—C13—C12	120.2 (2)
O1—C7—N1	125.6 (2)	C14—C13—H13	119.9
O1—C7—C8	129.6 (2)	C12—C13—H13	119.9
N1—C7—C8	104.77 (18)	C15—C16—C17	120.3 (2)
C17—C12—C13	119.5 (2)	C15—C16—H16	119.8
C17—C12—C11	120.9 (2)	C17—C16—H16	119.8
C13—C12—C11	119.66 (19)	C6—C5—C4	120.0 (3)
C9—N2—N1	106.44 (17)	C6—C5—H5	120.0
C11—N3—C18	128.4 (2)	C4—C5—H5	120.0
C11—N3—H3A	115.8	N3—C18—C19	111.5 (2)
C18—N3—H3A	115.8	N3—C18—H18A	109.3
N3—C11—C8	119.03 (19)	C19—C18—H18A	109.3
N3—C11—C12	118.1 (2)	N3—C18—H18B	109.3
C8—C11—C12	122.84 (18)	C19—C18—H18B	109.3
C19—N4—C19i	116.1 (3)	H18A—C18—H18B	108.0
C19—N4—H4	122.0	C13—C14—C15	119.9 (3)
C19i—N4—H4	122.0	C13—C14—H14	120.1
C11—C8—C7	122.52 (18)	C15—C14—H14	120.1
C11—C8—C9	130.9 (2)	C9—C10—H10A	109.5
C7—C8—C9	105.7 (2)	C9—C10—H10B	109.5
C5—C6—C1	119.9 (2)	H10A—C10—H10B	109.5
C5—C6—N1	120.5 (2)	C9—C10—H10C	109.5
C1—C6—N1	119.6 (2)	H10A—C10—H10C	109.5
C16—C17—C12	120.0 (2)	H10B—C10—H10C	109.5
C16—C17—H17	120.0	C2—C1—C6	118.8 (3)
C12—C17—H17	120.0	C2—C1—H1	120.6
N2—C9—C8	111.3 (2)	C6—C1—H1	120.6
N2—C9—C10	118.7 (2)	C3—C2—C1	121.6 (3)
C8—C9—C10	130.0 (2)	C3—C2—H2	119.2
N4—C19—C18	111.1 (2)	C1—C2—H2	119.2
N4—C19—H19A	109.4	C3—C4—C5	120.4 (3)
C18—C19—H19A	109.4	C3—C4—H4A	119.8
N4—C19—H19B	109.4	C5—C4—H4A	119.8
C18—C19—H19B	109.4	C2—C3—C4	119.1 (3)
H19A—C19—H19B	108.0	C2—C3—H3	120.4
C16—C15—C14	120.1 (2)	C4—C3—H3	120.4
N2—N1—C7—O1	176.4 (2)	C11—C12—C17—C16	−177.64 (19)
C6—N1—C7—O1	11.4 (3)	N1—N2—C9—C8	−1.4 (2)
N2—N1—C7—C8	−2.4 (2)	N1—N2—C9—C10	−179.79 (19)
C6—N1—C7—C8	−167.39 (18)	C11—C8—C9—N2	−168.8 (2)
C7—N1—N2—C9	2.5 (2)	C7—C8—C9—N2	0.0 (2)
C6—N1—N2—C9	169.01 (18)	C11—C8—C9—C10	9.3 (4)
C18—N3—C11—C8	−178.9 (2)	C7—C8—C9—C10	178.1 (2)
C18—N3—C11—C12	−0.7 (3)	C19i—N4—C19—C18	−172.3 (2)
C17—C12—C11—N3	−69.2 (3)	C17—C12—C13—C14	0.1 (4)
C13—C12—C11—N3	112.2 (2)	C11—C12—C13—C14	178.8 (2)
C17—C12—C11—C8	108.9 (2)	C14—C15—C16—C17	−0.1 (4)
C13—C12—C11—C8	−69.7 (3)	C12—C17—C16—C15	−1.0 (3)
N3—C11—C8—C7	−0.3 (3)	C1—C6—C5—C4	−1.8 (3)
C12—C11—C8—C7	−178.43 (19)	N1—C6—C5—C4	177.1 (2)
N3—C11—C8—C9	166.9 (2)	C11—N3—C18—C19	−135.6 (3)
C12—C11—C8—C9	−11.2 (3)	N4—C19—C18—N3	−52.7 (3)
O1—C7—C8—C11	−7.3 (4)	C12—C13—C14—C15	−1.3 (4)
N1—C7—C8—C11	171.45 (18)	C16—C15—C14—C13	1.3 (4)
O1—C7—C8—C9	−177.3 (2)	C5—C6—C1—C2	2.3 (3)
N1—C7—C8—C9	1.4 (2)	N1—C6—C1—C2	−176.6 (2)
C7—N1—C6—C5	−32.3 (3)	C6—C1—C2—C3	−1.3 (4)
N2—N1—C6—C5	163.56 (19)	C6—C5—C4—C3	0.3 (4)
C7—N1—C6—C1	146.5 (2)	C1—C2—C3—C4	−0.2 (5)
N2—N1—C6—C1	−17.5 (3)	C5—C4—C3—C2	0.7 (5)
C13—C12—C17—C16	1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.00	2.722 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	2.00	2.722 (2)	140