N'-[5-(4-Nitro-phen-yl)furan-2-yl-methyl-idene]-N,N-diphenyl-hydrazine.

The title compound, C(23)H(17)N(3)O(3), has an E configuration with respect to the C=N bond. The dihedral angle between the two phenyl rings bonded to the hydrazine group is 86.45 (13)°. The furan ring makes dihedral angles of 3.4 (2) and 7.06 (13)°, respectively, with the methyl-idenehydrazine C=N-N plane and the benzene ring.

Related literature

For applications of hydrazones, see: Kobotayeva et al. (2001 ▶); Barlow et al. (2000 ▶); Knight et al. (2000 ▶); Ros et al. (2008 ▶). For related structures, see: Clulow et al. (2008 ▶); Motherwell & Ramsay (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H17N3O3

M = 383.4

Monoclinic,

a = 16.815 (3) Å

b = 8.602 (1) Å

c = 13.340 (2) Å

β = 95.64 (2)°

V = 1920.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.4 × 0.4 × 0.15 mm

Data collection

Bruker P4 diffractometer

6417 measured reflections

5099 independent reflections

1970 reflections with I > 2σ(I)

R int = 0.067

3 standard reflections every 97 reflections intensity decay: 6%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.181

S = 0.97

5099 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: XSCANS (Siemens, 1994 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027388/is2572sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027388/is2572Isup2.hkl

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

C23H17N3O3	F(000) = 800
Mr = 383.4	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.815 (3) Å	Cell parameters from 48 reflections
b = 8.602 (1) Å	θ = 4.9–24.8°
c = 13.340 (2) Å	µ = 0.09 mm−1
β = 95.64 (2)°	T = 293 K
V = 1920.2 (6) Å3	Prism, red
Z = 4	0.4 × 0.4 × 0.15 mm

Bruker P4 diffractometer	Rint = 0.067
Radiation source: fine-focus sealed tube	θmax = 29°, θmin = 2.4°
graphite	h = −22→22
2θ/ω scans	k = −11→1
6417 measured reflections	l = −1→18
5099 independent reflections	3 standard reflections every 97 reflections
1970 reflections with I > 2σ(I)	intensity decay: 6%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0736P)2] where P = (Fo2 + 2Fc2)/3
5099 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.93074 (9)	0.17913 (18)	0.63960 (10)	0.0517 (4)
N2	0.78159 (11)	0.2996 (2)	0.63257 (14)	0.0538 (5)
C5	1.00087 (13)	0.0981 (3)	0.66001 (16)	0.0493 (6)
C6	1.05966 (13)	0.1186 (3)	0.58891 (17)	0.0501 (6)
C12	0.68625 (13)	0.4575 (3)	0.54061 (16)	0.0497 (6)
N1	0.70726 (11)	0.3624 (2)	0.62469 (14)	0.0570 (5)
N3	1.23249 (16)	0.1772 (3)	0.38172 (19)	0.0764 (7)
C1	0.80526 (14)	0.2131 (3)	0.70836 (17)	0.0525 (6)
H1	0.772	0.1957	0.759	0.063*
C9	1.17208 (15)	0.1553 (3)	0.45334 (18)	0.0610 (7)
C17	0.61353 (14)	0.5339 (3)	0.53010 (17)	0.0588 (7)
H17	0.5784	0.523	0.5793	0.071*
C18	0.65427 (13)	0.3410 (3)	0.70192 (17)	0.0511 (6)
C2	0.88302 (13)	0.1437 (3)	0.71450 (17)	0.0512 (6)
C13	0.73808 (15)	0.4766 (3)	0.46598 (17)	0.0586 (6)
H13	0.7872	0.426	0.4713	0.07*
O2	1.21847 (15)	0.2726 (3)	0.31372 (17)	0.0991 (8)
C7	1.12859 (15)	0.0287 (3)	0.59551 (19)	0.0657 (7)
H7	1.137	−0.0447	0.6467	0.079*
C15	0.64403 (16)	0.6445 (3)	0.37354 (18)	0.0629 (7)
H15	0.6299	0.706	0.3173	0.076*
O3	1.29323 (14)	0.1001 (3)	0.39341 (17)	0.1011 (8)
C4	0.99722 (14)	0.0144 (3)	0.74533 (18)	0.0578 (7)
H4	1.0369	−0.0506	0.7754	0.069*
C14	0.71625 (16)	0.5701 (3)	0.38482 (18)	0.0644 (7)
H14	0.7515	0.5835	0.336	0.077*
C16	0.59273 (15)	0.6266 (3)	0.44678 (19)	0.0629 (7)
H16	0.5436	0.6773	0.4403	0.075*
C11	1.04867 (16)	0.2261 (3)	0.51146 (18)	0.0645 (7)
H11	1.0027	0.2867	0.5052	0.077*
C10	1.10469 (18)	0.2449 (3)	0.44350 (19)	0.0708 (8)
H10	1.0967	0.3175	0.3918	0.085*
C3	0.92220 (14)	0.0439 (3)	0.78013 (18)	0.0597 (7)
H3	0.9032	0.0023	0.8376	0.072*
C23	0.60325 (16)	0.2166 (3)	0.6983 (2)	0.0636 (7)
H23	0.6024	0.1459	0.6455	0.076*
C22	0.55305 (16)	0.1962 (4)	0.7731 (2)	0.0742 (8)
H22	0.5183	0.1118	0.7707	0.089*
C20	0.60633 (17)	0.4242 (4)	0.8553 (2)	0.0742 (8)
H20	0.6078	0.494	0.9087	0.089*
C8	1.18501 (15)	0.0460 (4)	0.5276 (2)	0.0694 (7)
H8	1.2307	−0.0154	0.5323	0.083*
C19	0.65619 (15)	0.4447 (3)	0.78046 (18)	0.0626 (7)
H19	0.6911	0.5287	0.7831	0.075*
C21	0.55436 (17)	0.3006 (4)	0.8511 (2)	0.0774 (9)
H21	0.5201	0.2876	0.9011	0.093*

	U11	U22	U33	U12	U13	U23
O1	0.0515 (9)	0.0541 (10)	0.0499 (9)	0.0036 (8)	0.0077 (7)	0.0032 (8)
N2	0.0509 (12)	0.0572 (12)	0.0548 (12)	0.0066 (10)	0.0122 (9)	0.0004 (10)
C5	0.0488 (13)	0.0509 (14)	0.0478 (13)	0.0056 (11)	0.0033 (11)	−0.0031 (11)
C6	0.0510 (13)	0.0535 (15)	0.0459 (13)	−0.0033 (12)	0.0051 (10)	−0.0040 (12)
C12	0.0532 (14)	0.0521 (14)	0.0448 (12)	0.0028 (12)	0.0095 (10)	0.0012 (11)
N1	0.0516 (12)	0.0699 (14)	0.0521 (12)	0.0095 (11)	0.0176 (9)	0.0104 (11)
N3	0.0814 (18)	0.0832 (19)	0.0685 (16)	−0.0238 (16)	0.0271 (14)	−0.0264 (14)
C1	0.0529 (15)	0.0547 (14)	0.0512 (14)	0.0012 (12)	0.0118 (11)	0.0027 (12)
C9	0.0623 (16)	0.0718 (18)	0.0507 (14)	−0.0152 (14)	0.0146 (12)	−0.0119 (14)
C17	0.0580 (15)	0.0658 (17)	0.0546 (14)	0.0075 (13)	0.0152 (11)	0.0059 (13)
C18	0.0500 (13)	0.0559 (15)	0.0490 (13)	0.0054 (12)	0.0134 (11)	0.0083 (12)
C2	0.0530 (14)	0.0534 (14)	0.0484 (13)	−0.0013 (12)	0.0109 (11)	−0.0007 (12)
C13	0.0570 (14)	0.0664 (16)	0.0546 (14)	0.0056 (13)	0.0167 (11)	0.0031 (13)
O2	0.123 (2)	0.1055 (18)	0.0745 (13)	−0.0286 (15)	0.0401 (13)	−0.0019 (14)
C7	0.0621 (16)	0.0748 (18)	0.0616 (15)	0.0094 (14)	0.0135 (13)	0.0059 (14)
C15	0.0786 (19)	0.0553 (16)	0.0551 (15)	0.0026 (14)	0.0074 (13)	0.0089 (13)
O3	0.0833 (15)	0.117 (2)	0.1109 (17)	−0.0053 (15)	0.0475 (13)	−0.0214 (15)
C4	0.0601 (16)	0.0603 (16)	0.0531 (14)	0.0098 (13)	0.0060 (11)	0.0073 (13)
C14	0.0769 (18)	0.0642 (17)	0.0547 (15)	0.0022 (15)	0.0199 (13)	0.0056 (14)
C16	0.0627 (16)	0.0632 (17)	0.0633 (16)	0.0091 (13)	0.0092 (13)	0.0041 (14)
C11	0.0609 (17)	0.0750 (18)	0.0584 (15)	0.0047 (14)	0.0098 (13)	0.0042 (15)
C10	0.075 (2)	0.080 (2)	0.0583 (16)	−0.0018 (16)	0.0121 (14)	0.0087 (15)
C3	0.0635 (16)	0.0640 (16)	0.0530 (14)	0.0060 (14)	0.0125 (12)	0.0076 (13)
C23	0.0609 (16)	0.0618 (16)	0.0685 (16)	−0.0028 (14)	0.0087 (13)	0.0040 (14)
C22	0.0643 (18)	0.0710 (19)	0.088 (2)	−0.0119 (15)	0.0121 (15)	0.0219 (18)
C20	0.0856 (19)	0.079 (2)	0.0629 (17)	0.0042 (18)	0.0319 (14)	0.0024 (15)
C8	0.0588 (16)	0.083 (2)	0.0682 (17)	0.0069 (15)	0.0147 (13)	−0.0083 (16)
C19	0.0633 (16)	0.0639 (17)	0.0635 (16)	−0.0050 (14)	0.0205 (13)	0.0045 (14)
C21	0.0719 (19)	0.091 (2)	0.0750 (19)	0.0033 (18)	0.0346 (15)	0.0269 (18)

O1—C5	1.374 (2)	C13—H13	0.93
O1—C2	1.376 (3)	C7—C8	1.383 (3)
N2—C1	1.286 (3)	C7—H7	0.93
N2—N1	1.356 (3)	C15—C14	1.368 (3)
C5—C4	1.353 (3)	C15—C16	1.374 (3)
C5—C6	1.446 (3)	C15—H15	0.93
C6—C11	1.385 (3)	C4—C3	1.409 (3)
C6—C7	1.389 (3)	C4—H4	0.93
C12—C17	1.383 (3)	C14—H14	0.93
C12—C13	1.396 (3)	C16—H16	0.93
C12—N1	1.405 (3)	C11—C10	1.380 (4)
N1—C18	1.439 (3)	C11—H11	0.93
N3—O3	1.215 (3)	C10—H10	0.93
N3—O2	1.229 (3)	C3—H3	0.93
N3—C9	1.473 (3)	C23—C22	1.380 (4)
C1—C2	1.432 (3)	C23—H23	0.93
C1—H1	0.93	C22—C21	1.373 (4)
C9—C10	1.366 (4)	C22—H22	0.93
C9—C8	1.368 (4)	C20—C21	1.374 (4)
C17—C16	1.385 (3)	C20—C19	1.377 (3)
C17—H17	0.93	C20—H20	0.93
C18—C23	1.370 (3)	C8—H8	0.93
C18—C19	1.374 (3)	C19—H19	0.93
C2—C3	1.351 (3)	C21—H21	0.93
C13—C14	1.370 (3)
C5—O1—C2	107.12 (17)	C14—C15—H15	120.6
C1—N2—N1	120.19 (18)	C16—C15—H15	120.6
C4—C5—O1	109.13 (19)	C5—C4—C3	107.3 (2)
C4—C5—C6	135.0 (2)	C5—C4—H4	126.4
O1—C5—C6	115.92 (19)	C3—C4—H4	126.4
C11—C6—C7	117.9 (2)	C15—C14—C13	121.9 (2)
C11—C6—C5	121.4 (2)	C15—C14—H14	119.1
C7—C6—C5	120.7 (2)	C13—C14—H14	119.1
C17—C12—C13	118.7 (2)	C15—C16—C17	120.6 (2)
C17—C12—N1	120.5 (2)	C15—C16—H16	119.7
C13—C12—N1	120.8 (2)	C17—C16—H16	119.7
N2—N1—C12	116.83 (17)	C10—C11—C6	121.3 (3)
N2—N1—C18	121.64 (18)	C10—C11—H11	119.4
C12—N1—C18	121.41 (19)	C6—C11—H11	119.4
O3—N3—O2	123.9 (3)	C9—C10—C11	118.9 (3)
O3—N3—C9	118.1 (3)	C9—C10—H10	120.5
O2—N3—C9	118.0 (3)	C11—C10—H10	120.5
N2—C1—C2	119.7 (2)	C2—C3—C4	107.2 (2)
N2—C1—H1	120.1	C2—C3—H3	126.4
C2—C1—H1	120.1	C4—C3—H3	126.4
C10—C9—C8	121.9 (2)	C18—C23—C22	119.9 (3)
C10—C9—N3	118.9 (3)	C18—C23—H23	120
C8—C9—N3	119.1 (3)	C22—C23—H23	120
C12—C17—C16	120.4 (2)	C21—C22—C23	120.0 (3)
C12—C17—H17	119.8	C21—C22—H22	120
C16—C17—H17	119.8	C23—C22—H22	120
C23—C18—C19	120.1 (2)	C21—C20—C19	120.0 (3)
C23—C18—N1	120.3 (2)	C21—C20—H20	120
C19—C18—N1	119.6 (2)	C19—C20—H20	120
C3—C2—O1	109.2 (2)	C9—C8—C7	118.6 (3)
C3—C2—C1	133.3 (2)	C9—C8—H8	120.7
O1—C2—C1	117.4 (2)	C7—C8—H8	120.7
C14—C13—C12	119.7 (2)	C18—C19—C20	120.0 (3)
C14—C13—H13	120.2	C18—C19—H19	120
C12—C13—H13	120.2	C20—C19—H19	120
C8—C7—C6	121.4 (3)	C22—C21—C20	120.0 (3)
C8—C7—H7	119.3	C22—C21—H21	120
C6—C7—H7	119.3	C20—C21—H21	120
C14—C15—C16	118.8 (2)
C2—O1—C5—C4	0.0 (2)	N1—C12—C13—C14	−179.9 (2)
C2—O1—C5—C6	179.54 (19)	C11—C6—C7—C8	0.4 (4)
C4—C5—C6—C11	−174.0 (3)	C5—C6—C7—C8	179.5 (2)
O1—C5—C6—C11	6.6 (3)	O1—C5—C4—C3	−0.2 (3)
C4—C5—C6—C7	7.0 (4)	C6—C5—C4—C3	−179.6 (3)
O1—C5—C6—C7	−172.4 (2)	C16—C15—C14—C13	1.2 (4)
C1—N2—N1—C12	179.0 (2)	C12—C13—C14—C15	−1.0 (4)
C1—N2—N1—C18	2.9 (3)	C14—C15—C16—C17	−0.6 (4)
C17—C12—N1—N2	−175.9 (2)	C12—C17—C16—C15	−0.2 (4)
C13—C12—N1—N2	4.2 (3)	C7—C6—C11—C10	−0.7 (4)
C17—C12—N1—C18	0.2 (3)	C5—C6—C11—C10	−179.8 (2)
C13—C12—N1—C18	−179.7 (2)	C8—C9—C10—C11	1.0 (4)
N1—N2—C1—C2	178.2 (2)	N3—C9—C10—C11	−179.1 (2)
O3—N3—C9—C10	177.7 (2)	C6—C11—C10—C9	0.0 (4)
O2—N3—C9—C10	−2.2 (4)	O1—C2—C3—C4	−0.3 (3)
O3—N3—C9—C8	−2.4 (4)	C1—C2—C3—C4	178.6 (3)
O2—N3—C9—C8	177.7 (2)	C5—C4—C3—C2	0.3 (3)
C13—C12—C17—C16	0.4 (4)	C19—C18—C23—C22	0.7 (4)
N1—C12—C17—C16	−179.5 (2)	N1—C18—C23—C22	179.5 (2)
N2—N1—C18—C23	−89.7 (3)	C18—C23—C22—C21	−0.1 (4)
C12—N1—C18—C23	94.4 (3)	C10—C9—C8—C7	−1.3 (4)
N2—N1—C18—C19	89.1 (3)	N3—C9—C8—C7	178.8 (2)
C12—N1—C18—C19	−86.8 (3)	C6—C7—C8—C9	0.6 (4)
C5—O1—C2—C3	0.2 (2)	C23—C18—C19—C20	−0.5 (4)
C5—O1—C2—C1	−178.92 (19)	N1—C18—C19—C20	−179.3 (2)
N2—C1—C2—C3	−176.1 (3)	C21—C20—C19—C18	−0.4 (4)
N2—C1—C2—O1	2.7 (3)	C23—C22—C21—C20	−0.8 (4)
C17—C12—C13—C14	0.2 (4)	C19—C20—C21—C22	1.0 (4)