1-{(E)-[5-(2-Nitro-phen-yl)furan-2-yl]methyl-idene}-2,2-diphenyl-hydrazine.

In the title compound, C23H17N3O3, the terminal benzene rings are oriented at dihedral angles of 3.67 (7), 76.02 (7) and 16.37 (7)° with respect to the central furan ring. In the crystal, mol-ecules are connected via weak C-H⋯O hydrogen bonds, resulting in a three-dimensional supra-molecular array.

Related literature

For applications of hydrazones, see: Robinson (1963 ▶); Sztanke et al. (2007 ▶); Al-Macrosaur et al. (2007 ▶); Kucukguzel et al. (2003 ▶); Roma et al. (2000 ▶); Smalley et al. (2006 ▶); Gemma et al. (2006 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C23H17N3O3

M = 383.4

Monoclinic,

a = 11.2439 (2) Å

b = 17.3325 (4) Å

c = 19.7575 (4) Å

β = 105.778 (2)°

V = 3705.36 (13) Å3

Z = 8

Cu Kα radiation

μ = 0.76 mm−1

T = 130 K

0.58 × 0.23 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.759, T max = 0.892

12881 measured reflections

3395 independent reflections

3070 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.03

3395 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050246/xu5663sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050246/xu5663Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050246/xu5663Isup3.cml

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

C23H17N3O3	F(000) = 1600
Mr = 383.4	Dx = 1.375 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 11.2439 (2) Å	Cell parameters from 7112 reflections
b = 17.3325 (4) Å	θ = 4.7–68.0°
c = 19.7575 (4) Å	µ = 0.76 mm−1
β = 105.778 (2)°	T = 130 K
V = 3705.36 (13) Å3	Prism, dark red
Z = 8	0.58 × 0.23 × 0.16 mm

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	3395 independent reflections
Graphite monochromator	3070 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.025
ω scans	θmax = 68.1°, θmin = 4.7°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→12
Tmin = 0.759, Tmax = 0.892	k = −20→20
12881 measured reflections	l = −23→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0507P)2 + 2.4695P] where P = (Fo2 + 2Fc2)/3
3395 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.23 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
C1	0.78362 (12)	0.11751 (7)	0.50986 (6)	0.0257 (3)
C2	0.74740 (13)	0.14665 (8)	0.56708 (7)	0.0325 (3)
H2	0.672	0.1743	0.5597	0.039*
C3	0.82184 (16)	0.13506 (9)	0.63460 (8)	0.0413 (4)
H3	0.796	0.154	0.6734	0.05*
C4	0.93315 (15)	0.09646 (9)	0.64657 (7)	0.0409 (4)
H4	0.9841	0.0896	0.6931	0.049*
C5	0.96930 (14)	0.06805 (9)	0.59025 (7)	0.0357 (3)
H5	1.0458	0.0416	0.5981	0.043*
C6	0.89522 (12)	0.07768 (8)	0.52221 (7)	0.0300 (3)
H6	0.9206	0.0571	0.4838	0.036*
C7	0.74945 (11)	0.10332 (7)	0.38131 (6)	0.0241 (3)
C8	0.84143 (12)	0.14515 (7)	0.36340 (7)	0.0275 (3)
H8	0.8763	0.1892	0.3901	0.033*
C9	0.88229 (13)	0.12232 (9)	0.30637 (7)	0.0349 (3)
H9	0.946	0.1505	0.2943	0.042*
C10	0.83115 (14)	0.05903 (9)	0.26718 (7)	0.0374 (3)
H10	0.8599	0.0435	0.2283	0.045*
C11	0.73814 (15)	0.01799 (9)	0.28417 (8)	0.0401 (4)
H11	0.7021	−0.0252	0.2566	0.048*
C12	0.69702 (13)	0.03992 (8)	0.34186 (7)	0.0339 (3)
H12	0.6335	0.0115	0.354	0.041*
C13	0.53250 (12)	0.18208 (8)	0.37108 (7)	0.0289 (3)
H13	0.5551	0.1629	0.3312	0.035*
C14	0.42085 (12)	0.22646 (7)	0.36118 (7)	0.0277 (3)
C15	0.33253 (12)	0.24501 (8)	0.30155 (7)	0.0320 (3)
H15	0.3308	0.2304	0.2549	0.038*
C16	0.24368 (12)	0.29027 (8)	0.32204 (7)	0.0318 (3)
H16	0.1708	0.312	0.2919	0.038*
C17	0.28245 (11)	0.29681 (7)	0.39320 (7)	0.0259 (3)
C18	0.24109 (11)	0.33793 (7)	0.44712 (7)	0.0251 (3)
C19	0.32397 (12)	0.35087 (8)	0.51312 (7)	0.0307 (3)
H19	0.4049	0.3299	0.5228	0.037*
C20	0.29179 (13)	0.39311 (8)	0.56460 (7)	0.0352 (3)
H20	0.3503	0.4001	0.609	0.042*
C21	0.17507 (14)	0.42559 (8)	0.55249 (8)	0.0352 (3)
H21	0.1538	0.4553	0.5879	0.042*
C22	0.09046 (12)	0.41394 (7)	0.48811 (8)	0.0311 (3)
H22	0.0101	0.4358	0.4787	0.037*
C23	0.12323 (11)	0.37034 (7)	0.43747 (7)	0.0260 (3)
O2	−0.00013 (9)	0.29075 (6)	0.35265 (6)	0.0402 (3)
O3	−0.03133 (10)	0.41347 (7)	0.34252 (6)	0.0497 (3)
N1	0.70834 (10)	0.12687 (7)	0.44078 (6)	0.0295 (3)
N2	0.60193 (10)	0.16807 (6)	0.43303 (6)	0.0281 (2)
N3	0.02437 (10)	0.35707 (7)	0.37240 (6)	0.0304 (3)
O1	0.39230 (7)	0.25773 (5)	0.41814 (4)	0.0260 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0271 (7)	0.0272 (6)	0.0240 (6)	−0.0049 (5)	0.0089 (5)	0.0014 (5)
C2	0.0336 (7)	0.0356 (7)	0.0318 (7)	−0.0052 (6)	0.0147 (6)	−0.0051 (6)
C3	0.0538 (10)	0.0468 (9)	0.0273 (7)	−0.0110 (7)	0.0177 (7)	−0.0089 (6)
C4	0.0469 (9)	0.0488 (9)	0.0232 (7)	−0.0084 (7)	0.0032 (6)	0.0009 (6)
C5	0.0357 (8)	0.0394 (8)	0.0291 (7)	−0.0008 (6)	0.0040 (6)	0.0050 (6)
C6	0.0309 (7)	0.0349 (7)	0.0248 (6)	0.0013 (5)	0.0089 (5)	0.0012 (5)
C7	0.0206 (6)	0.0300 (6)	0.0213 (6)	0.0034 (5)	0.0052 (5)	0.0028 (5)
C8	0.0253 (6)	0.0293 (7)	0.0284 (6)	0.0004 (5)	0.0082 (5)	0.0003 (5)
C9	0.0347 (7)	0.0426 (8)	0.0327 (7)	0.0062 (6)	0.0179 (6)	0.0075 (6)
C10	0.0460 (8)	0.0447 (8)	0.0228 (7)	0.0175 (7)	0.0118 (6)	0.0037 (6)
C11	0.0470 (9)	0.0340 (8)	0.0320 (7)	0.0055 (6)	−0.0018 (6)	−0.0087 (6)
C12	0.0299 (7)	0.0325 (7)	0.0372 (7)	−0.0033 (6)	0.0054 (6)	0.0010 (6)
C13	0.0266 (7)	0.0331 (7)	0.0302 (7)	0.0003 (5)	0.0130 (5)	0.0030 (5)
C14	0.0256 (6)	0.0303 (7)	0.0293 (6)	−0.0001 (5)	0.0112 (5)	0.0019 (5)
C15	0.0308 (7)	0.0386 (7)	0.0272 (7)	0.0013 (6)	0.0086 (5)	0.0004 (5)
C16	0.0259 (7)	0.0382 (7)	0.0293 (7)	0.0038 (5)	0.0042 (5)	0.0038 (5)
C17	0.0193 (6)	0.0269 (6)	0.0301 (7)	0.0020 (5)	0.0044 (5)	0.0047 (5)
C18	0.0219 (6)	0.0236 (6)	0.0294 (6)	−0.0014 (5)	0.0065 (5)	0.0040 (5)
C19	0.0239 (6)	0.0352 (7)	0.0317 (7)	0.0000 (5)	0.0055 (5)	0.0012 (5)
C20	0.0339 (7)	0.0386 (8)	0.0314 (7)	−0.0058 (6)	0.0062 (6)	−0.0040 (6)
C21	0.0384 (8)	0.0309 (7)	0.0400 (8)	−0.0036 (6)	0.0171 (6)	−0.0056 (6)
C22	0.0269 (7)	0.0256 (6)	0.0429 (8)	0.0005 (5)	0.0130 (6)	0.0022 (6)
C23	0.0218 (6)	0.0226 (6)	0.0328 (7)	−0.0024 (5)	0.0060 (5)	0.0044 (5)
O2	0.0311 (5)	0.0397 (6)	0.0470 (6)	−0.0091 (4)	0.0057 (4)	−0.0080 (5)
O3	0.0318 (6)	0.0470 (6)	0.0595 (7)	0.0004 (5)	−0.0060 (5)	0.0201 (5)
N1	0.0242 (5)	0.0414 (6)	0.0251 (6)	0.0067 (5)	0.0103 (4)	0.0022 (5)
N2	0.0222 (5)	0.0328 (6)	0.0320 (6)	0.0025 (4)	0.0121 (4)	0.0039 (4)
N3	0.0195 (5)	0.0346 (6)	0.0367 (6)	−0.0019 (4)	0.0068 (5)	0.0060 (5)
O1	0.0208 (4)	0.0298 (5)	0.0271 (5)	0.0031 (3)	0.0060 (3)	0.0029 (3)

C1—C6	1.3943 (19)	C14—C15	1.3569 (19)
C1—C2	1.3961 (18)	C14—O1	1.3638 (15)
C1—N1	1.4062 (16)	C14—O1	1.3638 (15)
C2—C3	1.383 (2)	C15—C16	1.4133 (19)
C2—H2	0.95	C15—H15	0.95
C3—C4	1.382 (2)	C16—C17	1.3587 (19)
C3—H3	0.95	C16—H16	0.95
C4—C5	1.375 (2)	C17—O1	1.3770 (14)
C4—H4	0.95	C17—O1	1.3770 (14)
C5—C6	1.3856 (19)	C17—C18	1.4590 (18)
C5—H5	0.95	C18—C19	1.3994 (18)
C6—H6	0.95	C18—C23	1.4039 (18)
C7—C12	1.3830 (19)	C19—C20	1.379 (2)
C7—C8	1.3855 (18)	C19—H19	0.95
C7—N1	1.4340 (16)	C20—C21	1.388 (2)
C8—C9	1.3852 (18)	C20—H20	0.95
C8—H8	0.95	C21—C22	1.380 (2)
C9—C10	1.375 (2)	C21—H21	0.95
C9—H9	0.95	C22—C23	1.3814 (19)
C10—C11	1.380 (2)	C22—H22	0.95
C10—H10	0.95	C23—N3	1.4711 (17)
C11—C12	1.394 (2)	O2—O2	0
C11—H11	0.95	O2—N3	1.2212 (15)
C12—H12	0.95	O3—N3	1.2228 (15)
C13—N2	1.2833 (17)	N1—N2	1.3657 (15)
C13—C14	1.4396 (18)	N3—O2	1.2212 (15)
C13—H13	0.95	O1—O1	0.000 (3)
C6—C1—C2	118.96 (12)	C14—C15—C16	106.87 (12)
C6—C1—N1	120.17 (11)	C14—C15—H15	126.6
C2—C1—N1	120.86 (12)	C16—C15—H15	126.6
C3—C2—C1	119.68 (14)	C17—C16—C15	106.84 (12)
C3—C2—H2	120.2	C17—C16—H16	126.6
C1—C2—H2	120.2	C15—C16—H16	126.6
C4—C3—C2	121.18 (13)	C16—C17—O1	109.49 (11)
C4—C3—H3	119.4	C16—C17—O1	109.49 (11)
C2—C3—H3	119.4	O1—C17—O1	0.00 (9)
C5—C4—C3	119.22 (13)	C16—C17—C18	136.05 (12)
C5—C4—H4	120.4	O1—C17—C18	114.32 (10)
C3—C4—H4	120.4	O1—C17—C18	114.32 (10)
C4—C5—C6	120.65 (14)	C19—C18—C23	115.29 (12)
C4—C5—H5	119.7	C19—C18—C17	119.67 (11)
C6—C5—H5	119.7	C23—C18—C17	124.95 (11)
C5—C6—C1	120.29 (12)	C20—C19—C18	122.04 (13)
C5—C6—H6	119.9	C20—C19—H19	119
C1—C6—H6	119.9	C18—C19—H19	119
C12—C7—C8	120.34 (12)	C19—C20—C21	120.91 (13)
C12—C7—N1	120.33 (12)	C19—C20—H20	119.5
C8—C7—N1	119.32 (11)	C21—C20—H20	119.5
C9—C8—C7	119.61 (12)	C22—C21—C20	118.82 (13)
C9—C8—H8	120.2	C22—C21—H21	120.6
C7—C8—H8	120.2	C20—C21—H21	120.6
C10—C9—C8	120.36 (13)	C21—C22—C23	119.64 (12)
C10—C9—H9	119.8	C21—C22—H22	120.2
C8—C9—H9	119.8	C23—C22—H22	120.2
C9—C10—C11	120.18 (13)	C22—C23—C18	123.26 (12)
C9—C10—H10	119.9	C22—C23—N3	115.56 (11)
C11—C10—H10	119.9	C18—C23—N3	121.14 (11)
C10—C11—C12	120.01 (13)	O2—O2—N3	0 (10)
C10—C11—H11	120	N2—N1—C1	116.55 (10)
C12—C11—H11	120	N2—N1—C7	121.65 (10)
C7—C12—C11	119.48 (13)	C1—N1—C7	121.28 (10)
C7—C12—H12	120.3	C13—N2—N1	119.54 (11)
C11—C12—H12	120.3	O2—N3—O2	0.00 (15)
N2—C13—C14	120.83 (12)	O2—N3—O3	123.84 (12)
N2—C13—H13	119.6	O2—N3—O3	123.84 (12)
C14—C13—H13	119.6	O2—N3—C23	118.53 (11)
C15—C14—O1	109.97 (11)	O2—N3—C23	118.53 (11)
C15—C14—O1	109.97 (11)	O3—N3—C23	117.59 (11)
O1—C14—O1	0.00 (6)	O1—O1—C14	0 (10)
C15—C14—C13	130.53 (12)	O1—O1—C17	0 (10)
O1—C14—C13	119.50 (11)	C14—O1—C17	106.83 (9)
O1—C14—C13	119.50 (11)
C6—C1—C2—C3	−0.5 (2)	C20—C21—C22—C23	0.2 (2)
N1—C1—C2—C3	178.48 (12)	C21—C22—C23—C18	−1.6 (2)
C1—C2—C3—C4	1.4 (2)	C21—C22—C23—N3	176.22 (12)
C2—C3—C4—C5	−1.1 (2)	C19—C18—C23—C22	1.75 (18)
C3—C4—C5—C6	−0.2 (2)	C17—C18—C23—C22	−174.89 (12)
C4—C5—C6—C1	1.0 (2)	C19—C18—C23—N3	−175.97 (11)
C2—C1—C6—C5	−0.7 (2)	C17—C18—C23—N3	7.40 (19)
N1—C1—C6—C5	−179.69 (12)	C6—C1—N1—N2	−178.57 (11)
C12—C7—C8—C9	−1.14 (19)	C2—C1—N1—N2	2.45 (18)
N1—C7—C8—C9	179.46 (12)	C6—C1—N1—C7	−6.65 (18)
C7—C8—C9—C10	0.7 (2)	C2—C1—N1—C7	174.37 (12)
C8—C9—C10—C11	0.4 (2)	C12—C7—N1—N2	−79.10 (16)
C9—C10—C11—C12	−1.0 (2)	C8—C7—N1—N2	100.30 (14)
C8—C7—C12—C11	0.5 (2)	C12—C7—N1—C1	109.40 (14)
N1—C7—C12—C11	179.92 (12)	C8—C7—N1—C1	−71.20 (16)
C10—C11—C12—C7	0.5 (2)	C14—C13—N2—N1	−178.95 (11)
N2—C13—C14—C15	−176.81 (14)	C1—N1—N2—C13	176.38 (12)
N2—C13—C14—O1	3.82 (19)	C7—N1—N2—C13	4.49 (18)
N2—C13—C14—O1	3.82 (19)	O2—O2—N3—O3	0.00 (9)
O1—C14—C15—C16	−0.05 (15)	O2—O2—N3—C23	0.00 (10)
O1—C14—C15—C16	−0.05 (15)	C22—C23—N3—O2	−125.38 (13)
C13—C14—C15—C16	−179.46 (13)	C18—C23—N3—O2	52.50 (16)
C14—C15—C16—C17	−0.12 (16)	C22—C23—N3—O2	−125.38 (13)
C15—C16—C17—O1	0.24 (15)	C18—C23—N3—O2	52.50 (16)
C15—C16—C17—O1	0.24 (15)	C22—C23—N3—O3	52.21 (16)
C15—C16—C17—C18	175.53 (14)	C18—C23—N3—O3	−129.90 (13)
C16—C17—C18—C19	−159.87 (15)	C15—C14—O1—O1	0.00 (10)
O1—C17—C18—C19	15.26 (17)	C13—C14—O1—O1	0.00 (11)
O1—C17—C18—C19	15.26 (17)	C15—C14—O1—C17	0.20 (14)
C16—C17—C18—C23	16.6 (2)	O1—C14—O1—C17	0E1 (4)
O1—C17—C18—C23	−168.24 (11)	C13—C14—O1—C17	179.68 (11)
O1—C17—C18—C23	−168.24 (11)	C16—C17—O1—O1	0.00 (8)
C23—C18—C19—C20	−0.53 (19)	C18—C17—O1—O1	0.00 (9)
C17—C18—C19—C20	176.29 (12)	C16—C17—O1—C14	−0.27 (14)
C18—C19—C20—C21	−0.8 (2)	O1—C17—O1—C14	0E1 (4)
C19—C20—C21—C22	1.0 (2)	C18—C17—O1—C14	−176.69 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.95	2.48	3.1294 (16)	126
C9—H9···O2i	0.95	2.69	3.2324 (18)	117
C11—H11···O3ii	0.95	2.57	3.4336 (18)	151
C12—H12···O3iii	0.95	2.48	3.3786 (18)	158
C16—H16···O2	0.95	2.56	2.9635 (17)	106
C19—H19···O1	0.95	2.39	2.7389 (16)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.95	2.48	3.1294 (16)	126
C11—H11⋯O3ii	0.95	2.57	3.4336 (18)	151
C12—H12⋯O3iii	0.95	2.48	3.3786 (18)	158

Symmetry codes: (i) ; (ii) ; (iii) .