1-(4-Methyl-phenyl-diazo-nium-yl)-2-naphtholate.

In the title compound, C(17)H(14)N(2)O, the dihedral angle between the benzene ring and naphthalene ring system is 11.0 (3)°. The azo group adopts an anti configuration and an intra-molecular N-H⋯O hydrogen bond exists. Mol-ecules are packed by π-π inter-actions between adjacent mol-ecule (closest approach between centroids of benzene and naphthalene rings of 3.501 Å).

Related literature

For related literature, see: Lee et al. (2004 ▶); Oueslati et al. (2004 ▶); Wang et al. (2003 ▶).

Experimental

Crystal data

C17H14N2O

M = 262.30

Monoclinic,

a = 13.6740 (4) Å

b = 13.8000 (4) Å

c = 7.1430 (2) Å

β = 95.752 (2)°

V = 1341.11 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.992

14681 measured reflections

2913 independent reflections

1802 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.149

S = 1.04

2913 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064549/hj2006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064549/hj2006Isup2.hkl

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

C17H14N2O	F000 = 552
Mr = 262.30	Dx = 1.299 Mg m−3
Monoclinic, P2(1)/c	Melting point: 407 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 13.6740 (4) Å	Cell parameters from 2246 reflections
b = 13.8000 (4) Å	θ = 3.0–23.4º
c = 7.1430 (2) Å	µ = 0.08 mm−1
β = 95.752 (2)º	T = 293 (2) K
V = 1341.11 (7) Å3	Needle, red
Z = 4	0.20 × 0.10 × 0.10 mm

Bruker SMART Apex CCD area detector diffractometer	2913 independent reflections
Radiation source: fine-focus sealed tube	1802 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 293(2) K	θmax = 27.0º
phi and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.984, Tmax = 0.992	k = −17→16
14681 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0816P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2913 reflections	Δρmax = 0.18 e Å−3
185 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

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
C1	0.75809 (11)	−0.03170 (11)	0.1047 (2)	0.0516 (4)
C2	0.72115 (12)	−0.12434 (12)	0.0942 (3)	0.0649 (5)
H2	0.6535	−0.1342	0.0835	0.078*
C3	0.78410 (13)	−0.20284 (12)	0.0996 (3)	0.0687 (5)
H3	0.7580	−0.2651	0.0942	0.082*
C4	0.88439 (12)	−0.19111 (12)	0.1126 (2)	0.0574 (4)
C5	0.91975 (12)	−0.09723 (12)	0.1207 (2)	0.0641 (5)
H5	0.9873	−0.0872	0.1286	0.077*
C6	0.85837 (11)	−0.01801 (12)	0.1176 (2)	0.0611 (5)
H6	0.8844	0.0443	0.1241	0.073*
C7	0.65467 (11)	0.20510 (11)	0.1130 (2)	0.0508 (4)
C8	0.55267 (12)	0.18838 (12)	0.1327 (2)	0.0581 (4)
C9	0.49147 (13)	0.27144 (14)	0.1539 (2)	0.0689 (5)
H9	0.4253	0.2625	0.1690	0.083*
C10	0.52800 (13)	0.36158 (13)	0.1524 (2)	0.0689 (5)
H10	0.4860	0.4135	0.1667	0.083*
C11	0.62899 (12)	0.38124 (11)	0.1296 (2)	0.0580 (4)
C12	0.66538 (15)	0.47637 (13)	0.1275 (3)	0.0735 (5)
H12	0.6234	0.5282	0.1419	0.088*
C13	0.76133 (15)	0.49346 (13)	0.1045 (3)	0.0803 (6)
H13	0.7848	0.5567	0.1042	0.096*
C14	0.82436 (14)	0.41645 (13)	0.0816 (3)	0.0744 (5)
H14	0.8898	0.4284	0.0642	0.089*
C15	0.79103 (12)	0.32326 (12)	0.0843 (2)	0.0638 (5)
H15	0.8343	0.2725	0.0696	0.077*
C16	0.69297 (11)	0.30295 (11)	0.1089 (2)	0.0522 (4)
C17	0.95297 (13)	−0.27743 (13)	0.1212 (3)	0.0742 (5)
H17A	0.9433	−0.3159	0.2298	0.111*
H17B	1.0198	−0.2552	0.1295	0.111*
H17C	0.9393	−0.3159	0.0097	0.111*
N1	0.69010 (9)	0.04469 (9)	0.10377 (18)	0.0561 (4)
H1A	0.6116 (12)	0.0421 (10)	0.109 (2)	0.067*
N2	0.72155 (9)	0.13342 (9)	0.10388 (17)	0.0531 (4)
O1	0.51595 (8)	0.10306 (8)	0.13228 (18)	0.0726 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0530 (9)	0.0517 (9)	0.0499 (9)	0.0026 (7)	0.0044 (7)	0.0032 (7)
C2	0.0512 (9)	0.0586 (11)	0.0846 (13)	−0.0007 (8)	0.0055 (8)	0.0000 (9)
C3	0.0636 (11)	0.0507 (10)	0.0915 (14)	−0.0012 (8)	0.0071 (9)	−0.0010 (9)
C4	0.0636 (11)	0.0586 (11)	0.0506 (10)	0.0090 (8)	0.0090 (7)	0.0010 (7)
C5	0.0497 (9)	0.0699 (12)	0.0732 (12)	0.0028 (8)	0.0089 (8)	0.0042 (9)
C6	0.0538 (9)	0.0549 (10)	0.0749 (12)	−0.0034 (8)	0.0084 (8)	0.0030 (8)
C7	0.0528 (9)	0.0539 (10)	0.0449 (9)	0.0069 (7)	0.0005 (7)	0.0001 (7)
C8	0.0580 (10)	0.0647 (11)	0.0511 (10)	0.0056 (8)	0.0030 (7)	0.0014 (8)
C9	0.0545 (10)	0.0796 (13)	0.0727 (12)	0.0137 (9)	0.0069 (8)	−0.0056 (9)
C10	0.0704 (12)	0.0710 (12)	0.0646 (12)	0.0213 (9)	0.0029 (9)	−0.0069 (9)
C11	0.0690 (11)	0.0560 (10)	0.0471 (9)	0.0095 (8)	−0.0028 (7)	−0.0016 (7)
C12	0.0913 (14)	0.0554 (11)	0.0708 (12)	0.0138 (10)	−0.0060 (10)	−0.0029 (9)
C13	0.0980 (15)	0.0557 (12)	0.0844 (14)	−0.0077 (10)	−0.0045 (11)	0.0005 (9)
C14	0.0726 (12)	0.0633 (12)	0.0858 (13)	−0.0067 (9)	0.0014 (9)	0.0053 (10)
C15	0.0634 (11)	0.0575 (11)	0.0697 (12)	0.0017 (8)	0.0022 (8)	0.0010 (8)
C16	0.0571 (10)	0.0551 (10)	0.0430 (8)	0.0065 (7)	−0.0020 (7)	0.0000 (7)
C17	0.0766 (12)	0.0733 (12)	0.0735 (12)	0.0201 (9)	0.0111 (9)	−0.0002 (9)
N1	0.0504 (8)	0.0528 (9)	0.0650 (9)	0.0024 (6)	0.0056 (6)	0.0043 (6)
N2	0.0571 (8)	0.0510 (8)	0.0507 (8)	0.0023 (6)	0.0034 (6)	0.0015 (6)
O1	0.0574 (7)	0.0664 (8)	0.0945 (10)	−0.0048 (6)	0.0099 (6)	0.0028 (6)

C1—C2	1.374 (2)	C9—H9	0.9300
C1—C6	1.378 (2)	C10—C11	1.432 (2)
C1—N1	1.4051 (19)	C10—H10	0.9300
C2—C3	1.382 (2)	C11—C12	1.405 (2)
C2—H2	0.9300	C11—C16	1.407 (2)
C3—C4	1.375 (2)	C12—C13	1.359 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.382 (2)	C13—C14	1.388 (3)
C4—C17	1.513 (2)	C13—H13	0.9300
C5—C6	1.377 (2)	C14—C15	1.365 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.398 (2)
C7—N2	1.3531 (18)	C15—H15	0.9300
C7—C8	1.435 (2)	C17—H17A	0.9600
C7—C16	1.450 (2)	C17—H17B	0.9600
C8—O1	1.2799 (18)	C17—H17C	0.9600
C8—C9	1.436 (2)	N1—N2	1.2978 (16)
C9—C10	1.341 (2)	N1—H1A	1.078 (16)
C2—C1—C6	119.29 (14)	C11—C10—H10	118.6
C2—C1—N1	117.28 (14)	C12—C11—C16	119.45 (16)
C6—C1—N1	123.43 (14)	C12—C11—C10	121.66 (15)
C1—C2—C3	120.22 (15)	C16—C11—C10	118.89 (15)
C1—C2—H2	119.9	C13—C12—C11	120.72 (17)
C3—C2—H2	119.9	C13—C12—H12	119.6
C4—C3—C2	121.60 (15)	C11—C12—H12	119.6
C4—C3—H3	119.2	C12—C13—C14	119.98 (17)
C2—C3—H3	119.2	C12—C13—H13	120.0
C3—C4—C5	117.10 (14)	C14—C13—H13	120.0
C3—C4—C17	121.33 (15)	C15—C14—C13	120.49 (18)
C5—C4—C17	121.56 (15)	C15—C14—H14	119.8
C6—C5—C4	122.24 (15)	C13—C14—H14	119.8
C6—C5—H5	118.9	C14—C15—C16	121.10 (16)
C4—C5—H5	118.9	C14—C15—H15	119.5
C5—C6—C1	119.54 (15)	C16—C15—H15	119.5
C5—C6—H6	120.2	C15—C16—C11	118.26 (15)
C1—C6—H6	120.2	C15—C16—C7	122.84 (14)
N2—C7—C8	123.75 (14)	C11—C16—C7	118.90 (14)
N2—C7—C16	115.64 (13)	C4—C17—H17A	109.5
C8—C7—C16	120.57 (14)	C4—C17—H17B	109.5
O1—C8—C7	122.20 (14)	H17A—C17—H17B	109.5
O1—C8—C9	120.12 (15)	C4—C17—H17C	109.5
C7—C8—C9	117.68 (15)	H17A—C17—H17C	109.5
C10—C9—C8	121.20 (16)	H17B—C17—H17C	109.5
C10—C9—H9	119.4	N2—N1—C1	119.26 (13)
C8—C9—H9	119.4	N2—N1—H1A	111.2 (8)
C9—C10—C11	122.74 (15)	C1—N1—H1A	129.5 (8)
C9—C10—H10	118.6	N1—N2—C7	117.67 (13)
C6—C1—C2—C3	1.0 (3)	C10—C11—C12—C13	−179.58 (17)
N1—C1—C2—C3	−178.25 (14)	C11—C12—C13—C14	0.4 (3)
C1—C2—C3—C4	−1.0 (3)	C12—C13—C14—C15	−0.9 (3)
C2—C3—C4—C5	0.2 (3)	C13—C14—C15—C16	0.4 (3)
C2—C3—C4—C17	179.13 (15)	C14—C15—C16—C11	0.4 (2)
C3—C4—C5—C6	0.5 (3)	C14—C15—C16—C7	−179.87 (15)
C17—C4—C5—C6	−178.43 (15)	C12—C11—C16—C15	−0.8 (2)
C4—C5—C6—C1	−0.4 (3)	C10—C11—C16—C15	179.18 (14)
C2—C1—C6—C5	−0.3 (2)	C12—C11—C16—C7	179.46 (14)
N1—C1—C6—C5	178.88 (14)	C10—C11—C16—C7	−0.6 (2)
N2—C7—C8—O1	−4.1 (2)	N2—C7—C16—C15	4.2 (2)
C16—C7—C8—O1	178.26 (13)	C8—C7—C16—C15	−178.03 (14)
N2—C7—C8—C9	175.69 (14)	N2—C7—C16—C11	−176.08 (12)
C16—C7—C8—C9	−1.9 (2)	C8—C7—C16—C11	1.7 (2)
O1—C8—C9—C10	−179.15 (15)	C2—C1—N1—N2	−176.56 (13)
C7—C8—C9—C10	1.0 (2)	C6—C1—N1—N2	4.2 (2)
C8—C9—C10—C11	0.1 (3)	C1—N1—N2—C7	−176.60 (12)
C9—C10—C11—C12	179.64 (16)	C8—C7—N2—N1	3.5 (2)
C9—C10—C11—C16	−0.3 (2)	C16—C7—N2—N1	−178.79 (12)
C16—C11—C12—C13	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	1.078 (16)	1.578 (16)	2.5414 (16)	145.5 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	1.078 (16)	1.578 (16)	2.5414 (16)	145.5 (12)