4-[(4-Chloro-phen-yl)diazen-yl]-3-meth-oxy-aniline.

The title compound, C(13)H(12)ClN(3)O, exhibits a trans geometry about the N=N double bond in the solid state. The dihedral angle between the rings is 22.20 (8)°. Inter-molecular N-H⋯O hydrogen bonds between the amine and meth-oxy groups lead to the formation of a chain-like polymer along the c axis with a C(6) graph set. There is also weak non-classical C-H⋯N hydrogen bonds involving an aromatic C-H group and a diazenyl N atom, which connect the chains into a two-dimensional framework.

Related literature

For applications of diazo­nium compounds, see: Patai (1978 ▶); Hunger et al. (2005 ▶). For the synthesis and crystal structures of Hg(II) and Cd(II) complexes with [1,3-bis­(2-meth­oxy­phen­yl)]triazene, see: Rofouei, Hematyar et al. (2009 ▶); Rofouei, Melardi et al. (2009 ▶).

Experimental

Crystal data

C13H12ClN3O

M = 261.71

Monoclinic,

a = 15.398 (2) Å

b = 12.132 (2) Å

c = 14.276 (2) Å

β = 107.65 (1)°

V = 2541.3 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.30 × 0.17 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.698, T max = 0.746

42735 measured reflections

2778 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.118

S = 1.04

2778 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102472X/bh2358sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102472X/bh2358Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102472X/bh2358Isup3.cml

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

C13H12ClN3O	F(000) = 1088
Mr = 261.71	Dx = 1.368 Mg m−3
Monoclinic, C2/c	Melting point: 464 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 15.398 (2) Å	Cell parameters from 9801 reflections
b = 12.132 (2) Å	θ = 2.4–31.8°
c = 14.276 (2) Å	µ = 0.29 mm−1
β = 107.65 (1)°	T = 293 K
V = 2541.3 (7) Å3	Irregular, red
Z = 8	0.30 × 0.17 × 0.11 mm

Bruker APEXII CCD diffractometer	2778 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
Tmin = 0.698, Tmax = 0.746	k = −15→15
42735 measured reflections	l = −18→18

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.063P)2 + 1.2073P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2778 reflections	Δρmax = 0.37 e Å−3
172 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0021 (6)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Cl	0.38256 (4)	0.12838 (5)	0.25280 (3)	0.0899 (2)
N2	0.61207 (7)	0.40377 (9)	0.64610 (8)	0.0428 (3)
O	0.72867 (7)	0.56731 (8)	0.66289 (7)	0.0538 (3)
N3	0.56583 (8)	0.31792 (9)	0.64438 (8)	0.0450 (3)
C8	0.70965 (9)	0.53992 (11)	0.74685 (9)	0.0425 (3)
C1	0.52338 (9)	0.27653 (11)	0.54826 (9)	0.0435 (3)
C7	0.64918 (9)	0.45106 (10)	0.73903 (9)	0.0401 (3)
C9	0.74743 (10)	0.59254 (12)	0.83601 (10)	0.0478 (3)
H9	0.7869	0.6517	0.8403	0.057*
C11	0.66611 (10)	0.46804 (12)	0.91223 (10)	0.0485 (3)
H11	0.6520	0.4436	0.9676	0.058*
C10	0.72618 (10)	0.55670 (12)	0.91959 (10)	0.0484 (3)
C12	0.62817 (9)	0.41745 (11)	0.82355 (10)	0.0437 (3)
H12	0.5876	0.3595	0.8193	0.052*
C6	0.51547 (11)	0.33586 (13)	0.46265 (11)	0.0543 (4)
H6	0.5398	0.4065	0.4665	0.065*
N1	0.76334 (13)	0.60746 (16)	1.00811 (11)	0.0723 (5)
C2	0.48455 (12)	0.17279 (13)	0.54185 (12)	0.0590 (4)
H2	0.4879	0.1338	0.5989	0.071*
C3	0.44078 (12)	0.12672 (14)	0.45107 (13)	0.0658 (4)
H3	0.4150	0.0569	0.4467	0.079*
C4	0.43604 (11)	0.18557 (15)	0.36754 (12)	0.0589 (4)
C5	0.47166 (12)	0.29024 (15)	0.37226 (11)	0.0619 (4)
H5	0.4662	0.3298	0.3150	0.074*
C13	0.78626 (14)	0.65978 (16)	0.66487 (13)	0.0711 (5)
H13A	0.7942	0.6693	0.6012	0.107*
H13B	0.8445	0.6475	0.7128	0.107*
H13C	0.7589	0.7248	0.6820	0.107*
H1A	0.7476 (16)	0.5869 (19)	1.0576 (17)	0.085 (7)*
H1B	0.8002 (15)	0.6559 (18)	1.0126 (16)	0.075 (6)*

	U11	U22	U33	U12	U13	U23
Cl	0.0833 (4)	0.1190 (5)	0.0584 (3)	−0.0405 (3)	0.0080 (2)	−0.0312 (3)
N2	0.0442 (6)	0.0463 (6)	0.0377 (5)	−0.0031 (5)	0.0120 (4)	−0.0040 (4)
O	0.0662 (6)	0.0603 (6)	0.0355 (5)	−0.0191 (5)	0.0165 (4)	−0.0016 (4)
N3	0.0482 (6)	0.0454 (6)	0.0411 (6)	−0.0018 (5)	0.0130 (5)	−0.0032 (5)
C8	0.0470 (7)	0.0462 (7)	0.0343 (6)	−0.0015 (5)	0.0124 (5)	0.0004 (5)
C1	0.0411 (6)	0.0464 (7)	0.0425 (7)	−0.0017 (5)	0.0119 (5)	−0.0056 (5)
C7	0.0422 (6)	0.0428 (6)	0.0349 (6)	0.0011 (5)	0.0111 (5)	−0.0018 (5)
C9	0.0527 (7)	0.0489 (7)	0.0398 (7)	−0.0073 (6)	0.0111 (6)	−0.0038 (5)
C11	0.0585 (8)	0.0537 (7)	0.0369 (6)	0.0023 (6)	0.0197 (6)	0.0009 (5)
C10	0.0554 (8)	0.0524 (7)	0.0353 (6)	0.0022 (6)	0.0108 (6)	−0.0056 (5)
C12	0.0474 (7)	0.0444 (6)	0.0416 (6)	0.0002 (5)	0.0170 (5)	−0.0001 (5)
C6	0.0602 (8)	0.0547 (8)	0.0457 (7)	−0.0124 (7)	0.0126 (6)	−0.0032 (6)
N1	0.0930 (12)	0.0832 (11)	0.0395 (7)	−0.0252 (9)	0.0184 (7)	−0.0162 (7)
C2	0.0676 (9)	0.0545 (8)	0.0511 (8)	−0.0128 (7)	0.0121 (7)	0.0002 (6)
C3	0.0695 (10)	0.0576 (9)	0.0639 (10)	−0.0212 (8)	0.0105 (8)	−0.0104 (8)
C4	0.0496 (8)	0.0745 (10)	0.0481 (8)	−0.0131 (7)	0.0082 (6)	−0.0157 (7)
C5	0.0649 (9)	0.0738 (10)	0.0433 (7)	−0.0153 (8)	0.0110 (7)	−0.0027 (7)
C13	0.0866 (12)	0.0760 (11)	0.0548 (9)	−0.0334 (10)	0.0275 (9)	−0.0008 (8)

Cl—C4	1.7391 (16)	C10—N1	1.3657 (19)
N2—N3	1.2578 (16)	C12—H12	0.9300
N2—C7	1.3985 (16)	C6—C5	1.378 (2)
O—C8	1.3586 (16)	C6—H6	0.9300
O—C13	1.4250 (18)	N1—H1B	0.81 (2)
N3—C1	1.4206 (17)	N1—H1A	0.85 (2)
C8—C9	1.3846 (18)	C2—C3	1.384 (2)
C8—C7	1.4065 (18)	C2—H2	0.9300
C1—C2	1.384 (2)	C3—C4	1.373 (2)
C1—C6	1.392 (2)	C3—H3	0.9300
C7—C12	1.4014 (18)	C4—C5	1.377 (2)
C9—C10	1.3987 (19)	C5—H5	0.9300
C9—H9	0.9300	C13—H13A	0.9600
C11—C12	1.3683 (19)	C13—H13B	0.9600
C11—C10	1.402 (2)	C13—H13C	0.9600
C11—H11	0.9300
N3—N2—C7	115.10 (11)	C5—C6—C1	120.16 (14)
C8—O—C13	118.32 (11)	C5—C6—H6	119.9
N2—N3—C1	113.79 (11)	C1—C6—H6	119.9
O—C8—C9	123.74 (12)	C10—N1—H1B	119.4 (16)
O—C8—C7	115.59 (11)	C10—N1—H1A	119.5 (16)
C9—C8—C7	120.65 (12)	H1B—N1—H1A	121 (2)
C2—C1—C6	119.42 (13)	C3—C2—C1	120.45 (15)
C2—C1—N3	116.62 (13)	C3—C2—H2	119.8
C6—C1—N3	123.89 (12)	C1—C2—H2	119.8
N2—C7—C12	124.25 (12)	C4—C3—C2	119.06 (15)
N2—C7—C8	117.38 (11)	C4—C3—H3	120.5
C12—C7—C8	118.34 (11)	C2—C3—H3	120.5
C8—C9—C10	119.94 (13)	C3—C4—C5	121.45 (14)
C8—C9—H9	120.0	C3—C4—Cl	119.73 (13)
C10—C9—H9	120.0	C5—C4—Cl	118.81 (13)
C12—C11—C10	120.03 (12)	C4—C5—C6	119.40 (15)
C12—C11—H11	120.0	C4—C5—H5	120.3
C10—C11—H11	120.0	C6—C5—H5	120.3
N1—C10—C9	120.56 (15)	O—C13—H13A	109.5
N1—C10—C11	119.81 (14)	O—C13—H13B	109.5
C9—C10—C11	119.63 (12)	H13A—C13—H13B	109.5
C11—C12—C7	121.39 (13)	O—C13—H13C	109.5
C11—C12—H12	119.3	H13A—C13—H13C	109.5
C7—C12—H12	119.3	H13B—C13—H13C	109.5
C7—N2—N3—C1	175.50 (10)	C12—C11—C10—N1	179.51 (15)
C13—O—C8—C9	−4.1 (2)	C12—C11—C10—C9	−0.4 (2)
C13—O—C8—C7	177.23 (14)	C10—C11—C12—C7	1.1 (2)
N2—N3—C1—C2	169.37 (13)	N2—C7—C12—C11	−179.24 (12)
N2—N3—C1—C6	−13.7 (2)	C8—C7—C12—C11	−1.0 (2)
N3—N2—C7—C12	−8.56 (19)	C2—C1—C6—C5	−1.9 (2)
N3—N2—C7—C8	173.14 (11)	N3—C1—C6—C5	−178.75 (14)
O—C8—C7—N2	−2.78 (18)	C6—C1—C2—C3	2.1 (2)
C9—C8—C7—N2	178.49 (12)	N3—C1—C2—C3	179.20 (15)
O—C8—C7—C12	178.82 (12)	C1—C2—C3—C4	−0.3 (3)
C9—C8—C7—C12	0.1 (2)	C2—C3—C4—C5	−1.7 (3)
O—C8—C9—C10	−178.02 (13)	C2—C3—C4—Cl	179.22 (14)
C7—C8—C9—C10	0.6 (2)	C3—C4—C5—C6	2.0 (3)
C8—C9—C10—N1	179.64 (15)	Cl—C4—C5—C6	−178.99 (14)
C8—C9—C10—C11	−0.5 (2)	C1—C6—C5—C4	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Oi	0.85 (2)	2.47 (2)	3.222 (2)	147 (2)
C12—H12···N3ii	0.93	2.62	3.379 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Oi	0.85 (2)	2.47 (2)	3.222 (2)	147 (2)
C12—H12⋯N3ii	0.93	2.62	3.379 (2)	140

Symmetry codes: (i) ; (ii) .