Crystal structure of (E)-1-(2-nitro-benzyl-idene)-2,2-di-phenyl-hydrazine.

The title compound, C19H15N3O2, shows an E conformation of the imine bond. The dihedral angle between the planes of the phenyl rings in the di-phenyl-hydrazine groups is 88.52 (4)°. The 2-nitro-benzene ring shows a torsion angle of 10.17 (8)° with the C=N-N plane. A short intra-molecular C-H⋯O contact occurs. In the crystal, only van der Waals contacts occur between the mol-ecules.

Related literature

For background to hydrazide–hydrazone derivatives and their various biological activities, see: Sztanke et al. (2007 ▶); Al-Macrosaur et al. (2007 ▶); Roma et al. (2000 ▶); Smalley et al. (2006 ▶). For a related structure, see: Mendoza et al. (2012 ▶).

Experimental

Crystal data

C19H15N3O2

M = 317.34

Monoclinic,

a = 11.8536 (5) Å

b = 12.4293 (3) Å

c = 11.9492 (5) Å

β = 118.584 (5)°

V = 1545.92 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 140 K

0.59 × 0.49 × 0.27 mm

Data collection

Agilent Xcalibur Atlas Gemini diffractometer

Absorption correction: analytical (CrysAlis RED; Agilent, 2012 ▶) T min = 0.961, T max = 0.977

12199 measured reflections

3757 independent reflections

3057 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.03

3757 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis RED (Agilent, 2012 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, New_Global. DOI: 10.1107/S1600536814016109/hb7250sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016109/hb7250Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016109/hb7250Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016109/hb7250fig1.tif

The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as circles of arbitrary size.

Click here for additional data file.

. DOI: 10.1107/S1600536814016109/hb7250fig2.tif

The crystal packing in the title compound.

CCDC reference: 1013341

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H15N3O2	F(000) = 664
Mr = 317.34	Dx = 1.363 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6418 reflections
a = 11.8536 (5) Å	θ = 3.7–29.6°
b = 12.4293 (3) Å	µ = 0.09 mm−1
c = 11.9492 (5) Å	T = 140 K
β = 118.584 (5)°	Block, yellow
V = 1545.92 (12) Å3	0.59 × 0.49 × 0.27 mm
Z = 4

Agilent Xcalibur Atlas Gemini diffractometer	3757 independent reflections
Graphite monochromator	3057 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.023
ω scans	θmax = 29.6°, θmin = 3.7°
Absorption correction: analytical (CrysAlis RED; Agilent, 2012)	h = −15→15
Tmin = 0.961, Tmax = 0.977	k = −17→13
12199 measured reflections	l = −12→16

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.3936P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.19 e Å−3
3757 reflections	Δρmin = −0.29 e Å−3
217 parameters

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.

	x	y	z	Uiso*/Ueq
N2	0.11331 (9)	0.25147 (8)	0.92802 (9)	0.0231 (2)
N1	0.22974 (9)	0.29935 (8)	0.97008 (10)	0.0258 (2)
C1	0.23071 (11)	0.41296 (9)	0.97290 (10)	0.0222 (2)
C6	0.11903 (11)	0.47065 (9)	0.94355 (11)	0.0241 (2)
H6	0.042	0.4335	0.9251	0.029*
C13	0.10253 (11)	0.14893 (9)	0.91111 (11)	0.0228 (2)
H13	0.1743	0.1053	0.9263	0.027*
C5	0.12018 (12)	0.58203 (10)	0.94130 (11)	0.0269 (3)
H5	0.0434	0.6206	0.9203	0.032*
C18	−0.18121 (12)	−0.04581 (10)	0.79564 (12)	0.0306 (3)
H18	−0.1998	−0.1194	0.7728	0.037*
C14	−0.02595 (11)	0.10233 (9)	0.86714 (10)	0.0212 (2)
C4	0.23172 (12)	0.63796 (10)	0.96930 (12)	0.0286 (3)
H4	0.2315	0.7143	0.9655	0.034*
C9	0.53623 (12)	0.14688 (10)	1.11874 (12)	0.0304 (3)
H9	0.5981	0.1224	1.2007	0.037*
C15	−0.12374 (11)	0.16652 (10)	0.86682 (11)	0.0256 (3)
H15	−0.1055	0.2396	0.8923	0.031*
C12	0.35602 (11)	0.21828 (10)	0.87944 (11)	0.0267 (3)
H12	0.2942	0.2428	0.7974	0.032*
C7	0.34034 (10)	0.23976 (9)	0.98487 (11)	0.0222 (2)
C2	0.34400 (12)	0.46897 (10)	1.00538 (13)	0.0319 (3)
H2	0.4216	0.4308	1.0292	0.038*
C8	0.42978 (11)	0.20381 (10)	1.10458 (11)	0.0275 (3)
H8	0.4182	0.2181	1.1765	0.033*
O2	0.00953 (12)	−0.17689 (8)	0.82260 (11)	0.0517 (3)
N3	0.02964 (11)	−0.08055 (9)	0.81874 (10)	0.0347 (3)
C19	−0.06012 (11)	−0.00479 (9)	0.82864 (11)	0.0243 (2)
C16	−0.24502 (12)	0.12733 (11)	0.83091 (12)	0.0307 (3)
H16	−0.3091	0.1738	0.8299	0.037*
C10	0.55296 (12)	0.12539 (10)	1.01392 (13)	0.0289 (3)
H10	0.6262	0.0865	1.0239	0.035*
C11	0.46250 (12)	0.16084 (10)	0.89447 (12)	0.0302 (3)
H11	0.4735	0.1457	0.8224	0.036*
C17	−0.27406 (12)	0.02027 (11)	0.79614 (12)	0.0327 (3)
H17	−0.3572	−0.0071	0.7729	0.039*
O1	0.11844 (10)	−0.04545 (9)	0.80403 (12)	0.0537 (3)
C3	0.34333 (13)	0.58067 (11)	1.00287 (14)	0.0341 (3)
H3	0.4208	0.6183	1.0246	0.041*

	U11	U22	U33	U12	U13	U23
N2	0.0200 (5)	0.0234 (5)	0.0265 (5)	−0.0030 (4)	0.0115 (4)	−0.0025 (4)
N1	0.0186 (5)	0.0219 (5)	0.0368 (6)	−0.0018 (4)	0.0132 (4)	−0.0053 (4)
C1	0.0231 (6)	0.0214 (6)	0.0236 (6)	−0.0019 (4)	0.0125 (4)	−0.0041 (4)
C6	0.0207 (5)	0.0248 (6)	0.0261 (6)	−0.0023 (4)	0.0107 (4)	−0.0017 (4)
C13	0.0219 (6)	0.0217 (6)	0.0240 (6)	0.0016 (4)	0.0102 (4)	−0.0004 (4)
C5	0.0259 (6)	0.0259 (6)	0.0285 (6)	0.0030 (5)	0.0128 (5)	−0.0004 (5)
C18	0.0324 (7)	0.0234 (6)	0.0277 (6)	−0.0069 (5)	0.0077 (5)	−0.0010 (5)
C14	0.0228 (5)	0.0211 (5)	0.0190 (5)	−0.0007 (4)	0.0093 (4)	0.0006 (4)
C4	0.0352 (7)	0.0209 (6)	0.0340 (7)	−0.0026 (5)	0.0200 (6)	−0.0040 (5)
C9	0.0222 (6)	0.0298 (7)	0.0296 (7)	−0.0013 (5)	0.0047 (5)	0.0030 (5)
C15	0.0250 (6)	0.0237 (6)	0.0300 (6)	−0.0029 (5)	0.0147 (5)	−0.0039 (4)
C12	0.0238 (6)	0.0301 (6)	0.0245 (6)	0.0031 (5)	0.0102 (5)	0.0033 (5)
C7	0.0183 (5)	0.0192 (5)	0.0294 (6)	−0.0025 (4)	0.0117 (4)	−0.0035 (4)
C2	0.0250 (6)	0.0274 (6)	0.0483 (8)	−0.0028 (5)	0.0216 (6)	−0.0088 (5)
C8	0.0260 (6)	0.0303 (6)	0.0248 (6)	−0.0040 (5)	0.0110 (5)	−0.0045 (5)
O2	0.0655 (8)	0.0209 (5)	0.0550 (7)	0.0089 (5)	0.0178 (6)	−0.0016 (4)
N3	0.0321 (6)	0.0263 (6)	0.0322 (6)	0.0054 (5)	0.0045 (4)	−0.0066 (4)
C19	0.0259 (6)	0.0213 (5)	0.0210 (5)	0.0012 (5)	0.0074 (4)	0.0007 (4)
C16	0.0251 (6)	0.0342 (7)	0.0353 (7)	−0.0010 (5)	0.0165 (5)	−0.0025 (5)
C10	0.0208 (6)	0.0234 (6)	0.0418 (7)	0.0023 (5)	0.0145 (5)	0.0001 (5)
C11	0.0299 (6)	0.0326 (7)	0.0335 (7)	0.0012 (5)	0.0195 (5)	−0.0016 (5)
C17	0.0251 (6)	0.0369 (7)	0.0330 (7)	−0.0095 (5)	0.0113 (5)	−0.0003 (5)
O1	0.0338 (6)	0.0464 (6)	0.0806 (8)	−0.0013 (5)	0.0271 (6)	−0.0269 (6)
C3	0.0310 (7)	0.0294 (7)	0.0502 (8)	−0.0093 (5)	0.0261 (6)	−0.0103 (6)

N2—C13	1.2871 (15)	C9—H9	0.95
N2—N1	1.3593 (13)	C15—C16	1.3776 (17)
N1—C1	1.4125 (15)	C15—H15	0.95
N1—C7	1.4412 (14)	C12—C7	1.3845 (16)
C1—C2	1.3928 (16)	C12—C11	1.3849 (17)
C1—C6	1.3948 (16)	C12—H12	0.95
C6—C5	1.3849 (17)	C7—C8	1.3851 (16)
C6—H6	0.95	C2—C3	1.3887 (18)
C13—C14	1.4714 (15)	C2—H2	0.95
C13—H13	0.95	C8—H8	0.95
C5—C4	1.3856 (17)	O2—N3	1.2261 (15)
C5—H5	0.95	N3—O1	1.2274 (16)
C18—C17	1.3757 (19)	N3—C19	1.4674 (16)
C18—C19	1.3907 (17)	C16—C17	1.3874 (19)
C18—H18	0.95	C16—H16	0.95
C14—C19	1.4036 (16)	C10—C11	1.3844 (18)
C14—C15	1.4057 (16)	C10—H10	0.95
C4—C3	1.3821 (18)	C11—H11	0.95
C4—H4	0.95	C17—H17	0.95
C9—C10	1.3845 (18)	C3—H3	0.95
C9—C8	1.3846 (17)
C13—N2—N1	119.91 (10)	C7—C12—H12	120.3
N2—N1—C1	116.22 (9)	C11—C12—H12	120.3
N2—N1—C7	121.56 (9)	C12—C7—C8	120.52 (11)
C1—N1—C7	120.95 (9)	C12—C7—N1	119.85 (10)
C2—C1—C6	119.06 (11)	C8—C7—N1	119.63 (10)
C2—C1—N1	120.14 (10)	C3—C2—C1	119.92 (12)
C6—C1—N1	120.80 (10)	C3—C2—H2	120
C5—C6—C1	120.12 (11)	C1—C2—H2	120
C5—C6—H6	119.9	C9—C8—C7	119.57 (11)
C1—C6—H6	119.9	C9—C8—H8	120.2
N2—C13—C14	116.99 (10)	C7—C8—H8	120.2
N2—C13—H13	121.5	O2—N3—O1	123.23 (12)
C14—C13—H13	121.5	O2—N3—C19	117.53 (12)
C6—C5—C4	120.92 (11)	O1—N3—C19	119.22 (11)
C6—C5—H5	119.5	C18—C19—C14	122.52 (11)
C4—C5—H5	119.5	C18—C19—N3	115.57 (11)
C17—C18—C19	119.94 (11)	C14—C19—N3	121.90 (11)
C17—C18—H18	120	C15—C16—C17	120.31 (12)
C19—C18—H18	120	C15—C16—H16	119.8
C19—C14—C15	115.42 (10)	C17—C16—H16	119.8
C19—C14—C13	125.28 (10)	C11—C10—C9	119.72 (11)
C15—C14—C13	119.26 (10)	C11—C10—H10	120.1
C3—C4—C5	118.81 (11)	C9—C10—H10	120.1
C3—C4—H4	120.6	C10—C11—C12	120.40 (11)
C5—C4—H4	120.6	C10—C11—H11	119.8
C10—C9—C8	120.30 (11)	C12—C11—H11	119.8
C10—C9—H9	119.8	C18—C17—C16	119.32 (12)
C8—C9—H9	119.8	C18—C17—H17	120.3
C16—C15—C14	122.45 (11)	C16—C17—H17	120.3
C16—C15—H15	118.8	C4—C3—C2	121.07 (12)
C14—C15—H15	118.8	C4—C3—H3	119.5
C7—C12—C11	119.48 (11)	C2—C3—H3	119.5
C13—N2—N1—C1	173.38 (10)	N1—C1—C2—C3	177.32 (11)
C13—N2—N1—C7	6.11 (16)	C10—C9—C8—C7	−0.38 (18)
N2—N1—C1—C2	−175.12 (10)	C12—C7—C8—C9	0.64 (18)
C7—N1—C1—C2	−7.77 (16)	N1—C7—C8—C9	−179.78 (11)
N2—N1—C1—C6	4.95 (15)	C17—C18—C19—C14	2.08 (18)
C7—N1—C1—C6	172.30 (10)	C17—C18—C19—N3	−177.01 (11)
C2—C1—C6—C5	2.89 (17)	C15—C14—C19—C18	−1.66 (16)
N1—C1—C6—C5	−177.17 (11)	C13—C14—C19—C18	175.84 (11)
N1—N2—C13—C14	179.18 (9)	C15—C14—C19—N3	177.37 (10)
C1—C6—C5—C4	−0.71 (17)	C13—C14—C19—N3	−5.13 (17)
N2—C13—C14—C19	171.78 (11)	O2—N3—C19—C18	−22.36 (16)
N2—C13—C14—C15	−10.81 (16)	O1—N3—C19—C18	155.89 (12)
C6—C5—C4—C3	−1.63 (18)	O2—N3—C19—C14	158.54 (11)
C19—C14—C15—C16	−0.18 (17)	O1—N3—C19—C14	−23.21 (17)
C13—C14—C15—C16	−177.84 (11)	C14—C15—C16—C17	1.60 (19)
C11—C12—C7—C8	−0.34 (18)	C8—C9—C10—C11	−0.18 (19)
C11—C12—C7—N1	−179.92 (11)	C9—C10—C11—C12	0.48 (19)
N2—N1—C7—C12	80.11 (14)	C7—C12—C11—C10	−0.23 (19)
C1—N1—C7—C12	−86.56 (14)	C19—C18—C17—C16	−0.59 (19)
N2—N1—C7—C8	−99.47 (13)	C15—C16—C17—C18	−1.19 (19)
C1—N1—C7—C8	93.86 (13)	C5—C4—C3—C2	1.77 (19)
C6—C1—C2—C3	−2.75 (18)	C1—C2—C3—C4	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.95	2.27	2.7822 (15)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.95	2.27	2.7822 (15)	113