(E)-N-(3,3-Diphenyl-allyl-idene)-3-nitro-aniline.

In the title compound, C(21)H(16)N(2)O(2), the 3-nitro-phenyl and two phenyl rings are twisted from the mean plane of the enimino fragment by 44.4 (1), 37.2 (1) and 74.1 (1)°, respectively. The crystal packing exhibits no classical inter-molecular contacts.

Related literature

For the structure of (E)-N-(3,3-diphenylallylidene)-4-nitroaniline, see: Kang et al. (2012 ▶). For the crystal structures of other closely related compounds, see: Khalaji et al. (2008a ▶,b ▶).

Experimental

Crystal data

C21H16N2O2

M = 328.36

Monoclinic,

a = 5.8625 (7) Å

b = 22.825 (3) Å

c = 12.6370 (17) Å

β = 94.772 (4)°

V = 1685.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T min = 0.967, T max = 0.983

16270 measured reflections

3866 independent reflections

2663 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.136

S = 1.12

3866 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2006 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040354/cv5343sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040354/cv5343Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812040354/cv5343Isup3.cml

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

C21H16N2O2	F(000) = 688
Mr = 328.36	Dx = 1.294 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 8104 reflections
a = 5.8625 (7) Å	θ = 3.1–27.5°
b = 22.825 (3) Å	µ = 0.08 mm−1
c = 12.6370 (17) Å	T = 296 K
β = 94.772 (4)°	Block, colourless
V = 1685.1 (4) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3866 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 10.000 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −7→7
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	k = −29→29
Tmin = 0.967, Tmax = 0.983	l = −16→16
16270 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3
3866 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.2806 (3)	0.79532 (9)	0.84554 (13)	0.1205 (6)
O2	1.5869 (3)	0.74640 (6)	0.83527 (11)	0.0942 (5)
N1	1.14274 (19)	0.90554 (5)	0.51096 (9)	0.0464 (3)
N2	1.4414 (3)	0.78014 (6)	0.79813 (11)	0.0690 (4)
C1	0.5605 (3)	1.01496 (6)	0.15119 (11)	0.0525 (4)
H1	0.6562	1.0034	0.0999	0.063*
C2	0.3920 (3)	1.05589 (7)	0.12595 (13)	0.0613 (4)
H2	0.3776	1.0724	0.0584	0.074*
C3	0.2448 (3)	1.07259 (7)	0.19989 (13)	0.0573 (4)
H3	0.1292	1.0996	0.1820	0.069*
C4	0.2700 (2)	1.04891 (6)	0.30091 (12)	0.0506 (3)
H4	0.1717	1.0602	0.3513	0.061*
C5	0.4406 (2)	1.00859 (6)	0.32705 (11)	0.0452 (3)
H5	0.4567	0.9931	0.3953	0.054*
C6	0.5893 (2)	0.99065 (5)	0.25294 (10)	0.0405 (3)
C7	1.0213 (2)	0.90953 (7)	0.14288 (12)	0.0557 (4)
H7	1.1302	0.9376	0.1645	0.067*
C8	1.0584 (3)	0.87204 (8)	0.05913 (13)	0.0639 (4)
H8	1.1913	0.8756	0.0243	0.077*
C9	0.9005 (3)	0.82994 (7)	0.02771 (12)	0.0604 (4)
H9	0.9265	0.8050	−0.0282	0.072*
C10	0.7044 (3)	0.82455 (6)	0.07869 (13)	0.0594 (4)
H10	0.5979	0.7957	0.0580	0.071*
C11	0.6648 (2)	0.86225 (6)	0.16137 (11)	0.0510 (3)
H11	0.5306	0.8587	0.1953	0.061*
C12	0.8224 (2)	0.90501 (6)	0.19400 (10)	0.0410 (3)
C13	0.7721 (2)	0.94683 (5)	0.28026 (10)	0.0398 (3)
C14	0.8838 (2)	0.94559 (6)	0.37731 (10)	0.0442 (3)
H14	0.8489	0.9749	0.4245	0.053*
C15	1.0533 (2)	0.90295 (6)	0.41509 (10)	0.0443 (3)
H15	1.0975	0.8737	0.3699	0.053*
C16	1.3099 (2)	0.86430 (5)	0.54794 (10)	0.0410 (3)
C17	1.2973 (2)	0.84251 (6)	0.65043 (10)	0.0463 (3)
H17	1.1783	0.8536	0.6904	0.056*
C18	1.4632 (2)	0.80448 (6)	0.69138 (11)	0.0482 (3)
C19	1.6476 (2)	0.78813 (6)	0.63736 (13)	0.0539 (4)
H19	1.7594	0.7630	0.6678	0.065*
C20	1.6606 (2)	0.81029 (6)	0.53643 (13)	0.0554 (4)
H20	1.7835	0.8002	0.4981	0.067*
C21	1.4928 (2)	0.84741 (6)	0.49177 (11)	0.0495 (3)
H21	1.5026	0.8613	0.4231	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.1312 (13)	0.1592 (16)	0.0769 (10)	0.0438 (12)	0.0438 (10)	0.0502 (10)
O2	0.1215 (11)	0.0826 (9)	0.0741 (9)	0.0176 (8)	−0.0187 (8)	0.0249 (7)
N1	0.0500 (6)	0.0493 (6)	0.0393 (6)	0.0027 (5)	0.0002 (5)	0.0003 (5)
N2	0.0866 (10)	0.0658 (9)	0.0528 (8)	0.0040 (7)	−0.0050 (8)	0.0130 (7)
C1	0.0609 (8)	0.0564 (8)	0.0408 (7)	0.0120 (7)	0.0083 (6)	0.0034 (6)
C2	0.0769 (10)	0.0594 (9)	0.0473 (8)	0.0162 (8)	0.0031 (7)	0.0086 (7)
C3	0.0589 (8)	0.0508 (8)	0.0614 (9)	0.0128 (7)	0.0000 (7)	−0.0032 (7)
C4	0.0492 (7)	0.0508 (8)	0.0528 (8)	0.0019 (6)	0.0092 (6)	−0.0097 (6)
C5	0.0489 (7)	0.0467 (7)	0.0402 (7)	−0.0042 (6)	0.0051 (6)	−0.0033 (6)
C6	0.0439 (6)	0.0399 (6)	0.0375 (6)	−0.0028 (5)	0.0025 (5)	−0.0023 (5)
C7	0.0442 (7)	0.0690 (9)	0.0536 (8)	−0.0002 (7)	0.0027 (6)	−0.0100 (7)
C8	0.0522 (8)	0.0849 (11)	0.0549 (9)	0.0185 (8)	0.0053 (7)	−0.0081 (8)
C9	0.0762 (10)	0.0566 (9)	0.0464 (8)	0.0275 (8)	−0.0068 (8)	−0.0081 (7)
C10	0.0752 (10)	0.0443 (8)	0.0564 (9)	0.0008 (7)	−0.0073 (8)	−0.0059 (6)
C11	0.0552 (8)	0.0493 (8)	0.0483 (8)	−0.0040 (6)	0.0020 (6)	−0.0015 (6)
C12	0.0420 (6)	0.0421 (7)	0.0380 (7)	0.0047 (5)	−0.0019 (5)	0.0020 (5)
C13	0.0409 (6)	0.0403 (6)	0.0386 (6)	−0.0033 (5)	0.0051 (5)	0.0012 (5)
C14	0.0474 (7)	0.0443 (7)	0.0405 (7)	−0.0004 (6)	0.0010 (6)	−0.0019 (5)
C15	0.0479 (7)	0.0448 (7)	0.0400 (7)	−0.0032 (6)	0.0020 (6)	−0.0004 (5)
C16	0.0439 (6)	0.0415 (6)	0.0370 (6)	−0.0037 (5)	−0.0001 (5)	−0.0026 (5)
C17	0.0477 (7)	0.0519 (7)	0.0395 (7)	0.0006 (6)	0.0053 (6)	−0.0013 (6)
C18	0.0559 (7)	0.0451 (7)	0.0425 (7)	−0.0035 (6)	−0.0034 (6)	0.0011 (6)
C19	0.0528 (8)	0.0434 (7)	0.0637 (9)	0.0046 (6)	−0.0056 (7)	−0.0020 (6)
C20	0.0485 (7)	0.0523 (8)	0.0667 (10)	0.0017 (7)	0.0123 (7)	−0.0082 (7)
C21	0.0544 (7)	0.0502 (7)	0.0450 (7)	−0.0032 (6)	0.0094 (6)	−0.0004 (6)

O1—N2	1.209 (2)	C9—C10	1.369 (2)
O2—N2	1.2144 (18)	C9—H9	0.9300
N1—C15	1.2808 (16)	C10—C11	1.388 (2)
N1—C16	1.4101 (16)	C10—H10	0.9300
N2—C18	1.4742 (19)	C11—C12	1.3831 (19)
C1—C2	1.378 (2)	C11—H11	0.9300
C1—C6	1.3977 (18)	C12—C13	1.4965 (18)
C1—H1	0.9300	C13—C14	1.3419 (18)
C2—C3	1.378 (2)	C14—C15	1.4435 (18)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.383 (2)	C15—H15	0.9300
C3—H3	0.9300	C16—C21	1.3890 (19)
C4—C5	1.3792 (19)	C16—C17	1.3950 (18)
C4—H4	0.9300	C17—C18	1.3722 (19)
C5—C6	1.3930 (18)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.377 (2)
C6—C13	1.4852 (17)	C19—C20	1.380 (2)
C7—C12	1.383 (2)	C19—H19	0.9300
C7—C8	1.392 (2)	C20—C21	1.383 (2)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.370 (2)	C21—H21	0.9300
C8—H8	0.9300
C15—N1—C16	120.07 (12)	C12—C11—C10	120.85 (14)
O1—N2—O2	122.82 (15)	C12—C11—H11	119.6
O1—N2—C18	118.43 (14)	C10—C11—H11	119.6
O2—N2—C18	118.75 (16)	C7—C12—C11	118.79 (12)
C2—C1—C6	120.77 (13)	C7—C12—C13	121.17 (12)
C2—C1—H1	119.6	C11—C12—C13	119.99 (11)
C6—C1—H1	119.6	C14—C13—C6	120.97 (12)
C3—C2—C1	120.55 (14)	C14—C13—C12	122.78 (11)
C3—C2—H2	119.7	C6—C13—C12	116.25 (10)
C1—C2—H2	119.7	C13—C14—C15	125.94 (12)
C2—C3—C4	119.55 (13)	C13—C14—H14	117.0
C2—C3—H3	120.2	C15—C14—H14	117.0
C4—C3—H3	120.2	N1—C15—C14	119.87 (13)
C5—C4—C3	120.11 (13)	N1—C15—H15	120.1
C5—C4—H4	119.9	C14—C15—H15	120.1
C3—C4—H4	119.9	C21—C16—C17	118.56 (12)
C4—C5—C6	121.14 (13)	C21—C16—N1	124.11 (12)
C4—C5—H5	119.4	C17—C16—N1	117.18 (12)
C6—C5—H5	119.4	C18—C17—C16	119.03 (13)
C5—C6—C1	117.87 (12)	C18—C17—H17	120.5
C5—C6—C13	121.42 (12)	C16—C17—H17	120.5
C1—C6—C13	120.71 (12)	C17—C18—C19	123.04 (13)
C12—C7—C8	120.03 (14)	C17—C18—N2	118.09 (14)
C12—C7—H7	120.0	C19—C18—N2	118.87 (13)
C8—C7—H7	120.0	C18—C19—C20	117.71 (13)
C9—C8—C7	120.46 (15)	C18—C19—H19	121.1
C9—C8—H8	119.8	C20—C19—H19	121.1
C7—C8—H8	119.8	C21—C20—C19	120.63 (14)
C10—C9—C8	120.01 (14)	C21—C20—H20	119.7
C10—C9—H9	120.0	C19—C20—H20	119.7
C8—C9—H9	120.0	C20—C21—C16	120.99 (13)
C9—C10—C11	119.85 (14)	C20—C21—H21	119.5
C9—C10—H10	120.1	C16—C21—H21	119.5
C11—C10—H10	120.1
C6—C1—C2—C3	−1.6 (2)	C7—C12—C13—C6	107.60 (13)
C1—C2—C3—C4	1.4 (2)	C11—C12—C13—C6	−69.96 (15)
C2—C3—C4—C5	−0.4 (2)	C6—C13—C14—C15	175.77 (12)
C3—C4—C5—C6	−0.4 (2)	C12—C13—C14—C15	−4.3 (2)
C4—C5—C6—C1	0.18 (18)	C16—N1—C15—C14	−179.44 (11)
C4—C5—C6—C13	−179.42 (11)	C13—C14—C15—N1	−177.81 (13)
C2—C1—C6—C5	0.8 (2)	C15—N1—C16—C21	45.24 (18)
C2—C1—C6—C13	−179.58 (13)	C15—N1—C16—C17	−139.32 (13)
C12—C7—C8—C9	−1.0 (2)	C21—C16—C17—C18	−1.14 (18)
C7—C8—C9—C10	0.1 (2)	N1—C16—C17—C18	−176.83 (11)
C8—C9—C10—C11	0.7 (2)	C16—C17—C18—C19	2.3 (2)
C9—C10—C11—C12	−0.7 (2)	C16—C17—C18—N2	−177.55 (12)
C8—C7—C12—C11	1.0 (2)	O1—N2—C18—C17	−1.1 (2)
C8—C7—C12—C13	−176.60 (13)	O2—N2—C18—C17	179.95 (14)
C10—C11—C12—C7	−0.2 (2)	O1—N2—C18—C19	179.04 (17)
C10—C11—C12—C13	177.46 (12)	O2—N2—C18—C19	0.1 (2)
C5—C6—C13—C14	−36.10 (17)	C17—C18—C19—C20	−1.6 (2)
C1—C6—C13—C14	144.31 (14)	N2—C18—C19—C20	178.26 (12)
C5—C6—C13—C12	143.96 (12)	C18—C19—C20—C21	−0.3 (2)
C1—C6—C13—C12	−35.63 (16)	C19—C20—C21—C16	1.4 (2)
C7—C12—C13—C14	−72.33 (17)	C17—C16—C21—C20	−0.66 (19)
C11—C12—C13—C14	110.11 (14)	N1—C16—C21—C20	174.72 (11)