Crystal structure of 1-[(Z)-2-phenyl-hydrazin-1-yl-idene]naphthalen-2(1H)-one.

In the title compound, C16H12N2O, the dihedral angle between the planes of the benzene ring and naphthalenone ring system is 1.89 (8)°; an intra-molecular N-H⋯O hydrogen bond occurs between the imino group and the carbonyl group. In the crystal, mol-ecules are linked by weak C-H⋯π inter-actions into supra-molecular chains propagating along the [01-1] direction.

Related literature

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004 ▸); Oueslati et al. (2004 ▸).

Experimental

Crystal data

C16H12N2O

M = 248.28

Monoclinic,

a = 28.109 (5) Å

b = 6.039 (5) Å

c = 15.181 (5) Å

β = 103.243 (5)°

V = 2508 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.09 × 0.04 × 0.01 mm

Data collection

Bruker APEXII diffractometer

4481 measured reflections

2450 independent reflections

1469 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.169

S = 1.05

2450 reflections

176 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2006 ▸); cell refinement: SAINT (Bruker, 2006 ▸); data reduction: SAINT; 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 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006775/xu5845sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006775/xu5845Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006775/xu5845Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006775/xu5845fig1.tif

The mol­ecular structure of the title mol­ecule with the atom-numbering scheme. Ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

CCDC reference: 1057924

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

C16H12N2O	Z = 8
Mr = 248.28	F(000) = 1040
Monoclinic, C2/c	Dx = 1.315 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 28.109 (5) Å	µ = 0.08 mm−1
b = 6.039 (5) Å	T = 293 K
c = 15.181 (5) Å	Needle, red
β = 103.243 (5)°	0.09 × 0.04 × 0.01 mm
V = 2508 (2) Å3

Bruker APEXII diffractometer	Rint = 0.034
Horizonally mounted graphite crystal monochromator	θmax = 26.0°, θmin = 2.8°
CCD rotation images, thick slices scans	h = −33→34
4481 measured reflections	k = −7→7
2450 independent reflections	l = −18→18
1469 reflections with I > 2σ(I)

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.092P)2] where P = (Fo2 + 2Fc2)/3
2450 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.73024 (5)	0.6381 (3)	0.09280 (11)	0.0762 (6)
N1	0.65766 (7)	0.8669 (3)	0.00890 (12)	0.0551 (6)
N2	0.62773 (6)	0.7373 (2)	0.03831 (10)	0.0496 (5)
C1	0.63841 (7)	1.0493 (3)	−0.04642 (12)	0.0507 (6)
C2	0.58893 (8)	1.0917 (3)	−0.07177 (13)	0.0581 (7)
C3	0.57264 (9)	1.2751 (3)	−0.12414 (14)	0.0647 (8)
C4	0.60525 (10)	1.4165 (3)	−0.15058 (14)	0.0668 (9)
C5	0.65432 (10)	1.3745 (3)	−0.12602 (15)	0.0708 (9)
C6	0.67128 (8)	1.1886 (3)	−0.07340 (14)	0.0627 (8)
C7	0.64663 (7)	0.5645 (3)	0.09114 (12)	0.0474 (6)
C8	0.69840 (7)	0.5157 (3)	0.11735 (13)	0.0571 (7)
C9	0.71329 (8)	0.3216 (3)	0.17167 (14)	0.0663 (8)
C10	0.68014 (8)	0.1878 (3)	0.19510 (14)	0.0629 (8)
C12	0.59514 (8)	0.0806 (3)	0.19309 (14)	0.0618 (8)
C13	0.54622 (8)	0.1209 (3)	0.16897 (15)	0.0667 (8)
C14	0.52907 (8)	0.3124 (3)	0.12094 (14)	0.0642 (8)
C15	0.56100 (7)	0.4592 (3)	0.09687 (13)	0.0560 (7)
C16	0.61175 (7)	0.4199 (3)	0.11928 (12)	0.0465 (6)
C17	0.62863 (7)	0.2274 (3)	0.16940 (12)	0.0511 (6)
H1	0.6900 (5)	0.835 (4)	0.022 (2)	0.127 (11)*
H2	0.56680	0.99750	−0.05370	0.0700*
H3	0.53930	1.30370	−0.14180	0.0780*
H4	0.59390	1.54080	−0.18520	0.0800*
H5	0.67630	1.46940	−0.14430	0.0850*
H6	0.70460	1.15890	−0.05660	0.0750*
H9	0.74640	0.28840	0.19080	0.0800*
H10	0.69120	0.06310	0.22980	0.0750*
H12	0.60650	−0.04640	0.22580	0.0740*
H13	0.52430	0.02100	0.18450	0.0800*
H14	0.49570	0.34080	0.10510	0.0770*
H15	0.54900	0.58690	0.06520	0.0670*

	U11	U22	U33	U12	U13	U23
O1	0.0554 (9)	0.0765 (10)	0.0933 (12)	−0.0043 (7)	0.0103 (8)	0.0133 (8)
N1	0.0601 (11)	0.0475 (9)	0.0584 (11)	0.0026 (8)	0.0153 (9)	0.0031 (7)
N2	0.0601 (10)	0.0441 (8)	0.0455 (9)	0.0048 (7)	0.0139 (8)	−0.0013 (7)
C1	0.0666 (13)	0.0414 (9)	0.0457 (11)	0.0035 (9)	0.0160 (9)	−0.0021 (8)
C2	0.0695 (14)	0.0496 (11)	0.0568 (13)	0.0017 (9)	0.0180 (11)	0.0021 (9)
C3	0.0791 (15)	0.0538 (11)	0.0594 (13)	0.0129 (11)	0.0119 (12)	0.0008 (10)
C4	0.0995 (19)	0.0508 (11)	0.0515 (13)	0.0121 (12)	0.0201 (12)	0.0054 (9)
C5	0.1042 (19)	0.0529 (11)	0.0638 (14)	−0.0047 (12)	0.0371 (13)	0.0041 (10)
C6	0.0723 (14)	0.0594 (12)	0.0607 (13)	−0.0004 (10)	0.0244 (11)	0.0013 (10)
C7	0.0555 (11)	0.0441 (9)	0.0411 (10)	0.0051 (8)	0.0080 (9)	−0.0020 (8)
C8	0.0557 (13)	0.0568 (11)	0.0553 (12)	0.0009 (10)	0.0057 (10)	−0.0013 (9)
C9	0.0566 (13)	0.0693 (13)	0.0664 (14)	0.0093 (11)	0.0003 (11)	0.0102 (11)
C10	0.0722 (15)	0.0562 (12)	0.0566 (12)	0.0164 (10)	0.0069 (11)	0.0111 (10)
C12	0.0806 (16)	0.0512 (11)	0.0556 (12)	0.0085 (10)	0.0198 (11)	0.0076 (9)
C13	0.0737 (15)	0.0608 (12)	0.0719 (15)	−0.0033 (11)	0.0297 (12)	0.0048 (11)
C14	0.0583 (13)	0.0662 (13)	0.0704 (14)	0.0050 (10)	0.0195 (11)	0.0013 (11)
C15	0.0603 (13)	0.0524 (10)	0.0565 (12)	0.0098 (9)	0.0161 (10)	0.0056 (9)
C16	0.0568 (12)	0.0436 (9)	0.0394 (9)	0.0064 (8)	0.0117 (8)	−0.0039 (8)
C17	0.0627 (13)	0.0468 (10)	0.0438 (10)	0.0060 (9)	0.0123 (9)	−0.0011 (8)

O1—C8	1.280 (3)	C12—C13	1.361 (3)
N1—N2	1.301 (3)	C13—C14	1.393 (3)
N1—C1	1.415 (3)	C14—C15	1.369 (3)
N2—C7	1.349 (3)	C15—C16	1.409 (3)
N1—H1	0.906 (17)	C16—C17	1.411 (3)
C1—C2	1.379 (3)	C2—H2	0.9300
C1—C6	1.379 (3)	C3—H3	0.9300
C2—C3	1.379 (3)	C4—H4	0.9300
C3—C4	1.378 (4)	C5—H5	0.9300
C4—C5	1.368 (4)	C6—H6	0.9300
C5—C6	1.397 (3)	C9—H9	0.9300
C7—C8	1.448 (3)	C10—H10	0.9300
C7—C16	1.449 (3)	C12—H12	0.9300
C8—C9	1.439 (3)	C13—H13	0.9300
C9—C10	1.342 (3)	C14—H14	0.9300
C10—C17	1.431 (3)	C15—H15	0.9300
C12—C17	1.399 (3)
O1···N1	2.550 (3)	C4···H12iv	2.9200
O1···N2	2.873 (3)	C5···H12iv	3.0700
O1···H1	1.81 (2)	C8···H1	2.39 (3)
O1···H6i	2.7100	C12···H4vi	2.9400
N1···O1	2.550 (3)	C13···H4vi	3.0800
N1···C10ii	3.366 (4)	C14···H3v	3.0700
N2···O1	2.873 (3)	C17···H4vi	2.9600
N2···C4iii	3.398 (4)	H1···O1	1.81 (2)
N2···C12ii	3.412 (4)	H1···C8	2.39 (3)
N2···H2	2.5000	H1···H6	2.3800
N2···H15	2.5100	H2···N2	2.5000
C1···C16ii	3.572 (4)	H3···C14v	3.0700
C1···C17ii	3.519 (4)	H3···H14v	2.4800
C2···C16ii	3.450 (4)	H4···C12vii	2.9400
C4···N2ii	3.398 (4)	H4···C13vii	3.0800
C5···C7ii	3.544 (4)	H4···C17vii	2.9600
C6···C8ii	3.443 (4)	H6···H1	2.3800
C6···C7ii	3.559 (4)	H6···O1i	2.7100
C7···C5iii	3.544 (4)	H9···H10viii	2.5100
C7···C6iii	3.559 (4)	H10···H12	2.4600
C8···C6iii	3.443 (4)	H10···H9ix	2.5100
C10···N1iii	3.366 (4)	H12···H10	2.4600
C12···N2iii	3.412 (4)	H12···C3x	3.0000
C16···C1iii	3.572 (4)	H12···C4x	2.9200
C16···C2iii	3.450 (4)	H12···C5x	3.0700
C17···C1iii	3.519 (4)	H14···C3v	3.0700
C3···H12iv	3.0000	H14···H3v	2.4800
C3···H14v	3.0700	H15···N2	2.5100
N2—N1—C1	118.85 (18)	C7—C16—C15	122.93 (17)
N1—N2—C7	118.17 (17)	C12—C17—C16	119.86 (18)
N2—N1—H1	119.5 (16)	C10—C17—C12	121.51 (17)
C1—N1—H1	121.6 (16)	C10—C17—C16	118.63 (17)
N1—C1—C2	122.28 (18)	C1—C2—H2	120.00
N1—C1—C6	117.38 (18)	C3—C2—H2	120.00
C2—C1—C6	120.34 (18)	C2—C3—H3	120.00
C1—C2—C3	119.4 (2)	C4—C3—H3	120.00
C2—C3—C4	120.7 (2)	C3—C4—H4	120.00
C3—C4—C5	120.15 (19)	C5—C4—H4	120.00
C4—C5—C6	119.7 (2)	C4—C5—H5	120.00
C1—C6—C5	119.7 (2)	C6—C5—H5	120.00
C8—C7—C16	120.11 (16)	C1—C6—H6	120.00
N2—C7—C8	123.70 (17)	C5—C6—H6	120.00
N2—C7—C16	116.15 (17)	C8—C9—H9	120.00
C7—C8—C9	117.72 (18)	C10—C9—H9	120.00
O1—C8—C9	120.41 (19)	C9—C10—H10	118.00
O1—C8—C7	121.87 (17)	C17—C10—H10	118.00
C8—C9—C10	120.9 (2)	C13—C12—H12	120.00
C9—C10—C17	123.23 (18)	C17—C12—H12	119.00
C13—C12—C17	121.02 (18)	C12—C13—H13	120.00
C12—C13—C14	119.8 (2)	C14—C13—H13	120.00
C13—C14—C15	120.5 (2)	C13—C14—H14	120.00
C14—C15—C16	121.05 (18)	C15—C14—H14	120.00
C7—C16—C17	119.28 (18)	C14—C15—H15	119.00
C15—C16—C17	117.77 (17)	C16—C15—H15	119.00
C1—N1—N2—C7	−179.84 (16)	C8—C7—C16—C15	179.34 (17)
N2—N1—C1—C2	−1.4 (3)	C8—C7—C16—C17	−2.4 (3)
N2—N1—C1—C6	177.41 (17)	O1—C8—C9—C10	−177.61 (19)
N1—N2—C7—C8	0.3 (3)	C7—C8—C9—C10	1.7 (3)
N1—N2—C7—C16	−177.64 (16)	C8—C9—C10—C17	−0.6 (3)
N1—C1—C2—C3	178.57 (18)	C9—C10—C17—C12	178.22 (19)
C6—C1—C2—C3	−0.2 (3)	C9—C10—C17—C16	−2.0 (3)
N1—C1—C6—C5	−178.28 (18)	C17—C12—C13—C14	−0.8 (3)
C2—C1—C6—C5	0.5 (3)	C13—C12—C17—C10	179.41 (19)
C1—C2—C3—C4	−0.5 (3)	C13—C12—C17—C16	−0.4 (3)
C2—C3—C4—C5	0.9 (3)	C12—C13—C14—C15	0.8 (3)
C3—C4—C5—C6	−0.5 (3)	C13—C14—C15—C16	0.5 (3)
C4—C5—C6—C1	−0.2 (3)	C14—C15—C16—C7	176.67 (18)
N2—C7—C8—O1	1.2 (3)	C14—C15—C16—C17	−1.7 (3)
N2—C7—C8—C9	−178.06 (17)	C7—C16—C17—C10	3.4 (3)
C16—C7—C8—O1	179.10 (18)	C7—C16—C17—C12	−176.80 (17)
C16—C7—C8—C9	−0.2 (3)	C15—C16—C17—C10	−178.21 (17)
N2—C7—C16—C15	−2.6 (3)	C15—C16—C17—C12	1.6 (3)
N2—C7—C16—C17	175.67 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.906 (17)	1.81 (2)	2.550 (3)	137 (2)
C4—H4···Cg3vii	0.93	2.76	3.568 (4)	145
C12—H12···Cg1x	0.93	2.83	3.612 (4)	142

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg3 are the centroids of the C1C6 and C12C17 rings, respectively.

DHA	DH	HA	D A	DHA
N1H1O1	0.906(17)	1.81(2)	2.550(3)	137(2)
C4H4Cg3i	0.93	2.76	3.568(4)	145
C12H12Cg1ii	0.93	2.83	3.612(4)	142

Symmetry codes: (i) ; (ii) .