4-Chloro-2-(phenyl­diazenyl)­phenol from powder data: a form stable at room temperature

The low-temperature form of the title compound, C₁₂H₉ClN₂O, (I), was obtained from an ethanol solution of (I) at room temperature. The mol­ecule of (I) is almost planar; the dihedral angle formed by the planes of the phenyl rings is 5.0 (4)°. Translationally related mol­ecules form stacks with an interplanar separation of 3.32 (1) Å.

Key indicators

• Powder X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.027
• wR factor = 0.036

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: local program; cell refinement: LSPAID (Visser, 1986); program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to refine structure: MRIA; molecular graphics: PLUTON (Spek, 1992); software used to prepare material for publication: PARST (Nardelli, 1983).

4-chloro-2-(phenyldiazenyl)phenol

Crystal data

C12H9ClN2O	F(000) = 480
Mr = 232.66	Dx = 1.428 Mg m^−3
Monoclinic, P21/n	Melting point: 384 K
a = 19.706 (6) Å	Cu Kα radiation, λ = 1.5418 Å
b = 4.614 (2) Å	T = 295 K
c = 12.308 (4) Å	Particle morphology: needles
β = 104.70 (3)°	yellow
V = 1082.5 (7) Å^3	flat_sheet, 25 × 25 mm
Z = 4

Data collection

DRON-3M diffractometer (Burevestnik, Russia)	Data collection mode: reflection
Radiation source: X-ray sealed tube	Scan method: step
Ni filtered monochromator	2θmin = 7.0°, 2θmax = 70.0°, 2θstep = 0.02°
Specimen mounting: pressed as a thin layer in the specimen holder

Refinement

Refinement on Inet	115 parameters
Least-squares matrix: full with fixed elements per cycle	10 restraints
Rp = 0.027	0 constraints
Rwp = 0.036	H-atom parameters not refined
Rexp = 0.033	Weighting scheme based on measured s.u.'s
3251 data points	(Δ/σ)max = 0.034
Excluded region(s): 5.00 - 6.98	Background function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-Voigt	Preferred orientation correction: Spherical harmonics (Ahtee et al., 1989)

Special details

Experimental. specimen was rotated in its plane

Refinement. Hydrogen atoms were placed in calculated positions. The planarity of the phenyl groups was restrained.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3301 (4)	0.1422 (17)	−0.0883 (5)	0.071 (2)*
C2	0.3307 (3)	0.2377 (16)	0.0211 (4)	0.071 (2)*
C3	0.3778 (5)	0.114 (2)	0.1140 (3)	0.071 (2)*
C4	0.4237 (3)	−0.0995 (13)	0.0979 (4)	0.071 (2)*
C5	0.4240 (3)	−0.1936 (12)	−0.0122 (4)	0.071 (2)*
C6	0.3766 (4)	−0.0831 (16)	−0.1031 (3)	0.071 (2)*
N7	0.2847 (5)	0.458 (2)	0.0484 (6)	0.079 (2)*
N8	0.2414 (5)	0.589 (2)	−0.0271 (6)	0.079 (2)*
C9	0.1940 (4)	0.7929 (18)	0.0014 (3)	0.059 (2)*
C10	0.1453 (4)	0.9169 (19)	−0.0890 (3)	0.059 (2)*
C11	0.0969 (3)	1.1167 (15)	−0.0693 (3)	0.059 (2)*
C12	0.0955 (3)	1.1839 (15)	0.0404 (3)	0.059 (2)*
C13	0.1449 (3)	1.0619 (16)	0.1305 (3)	0.059 (2)*
C14	0.1942 (4)	0.8655 (18)	0.1111 (3)	0.059 (2)*
O1	0.2845 (3)	0.2679 (16)	−0.1764 (5)	0.079 (2)*
CL1	0.4827 (2)	−0.2461 (12)	0.2071 (3)	0.070 (4)
H1	0.2562	0.403	−0.1588	0.076*
H3	0.3789	0.185	0.1912	0.076*
H5	0.4573	−0.353	−0.0181	0.076*
H6	0.3742	−0.144	−0.1819	0.076*
H10	0.1464	0.868	−0.1676	0.076*
H11	0.0623	1.209	−0.1339	0.076*
H12	0.0611	1.329	0.0547	0.076*
H13	0.1448	1.115	0.2092	0.076*
H14	0.2288	0.774	0.1757	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
CL1	0.079 (5)	0.045 (7)	0.082 (5)	0.027 (7)	0.008 (5)	0.024 (5)

Geometric parameters (Å, º)

C1—C2	1.414 (8)	C12—C13	1.395 (7)
C1—C6	1.428 (11)	C13—C14	1.393 (10)
C2—C3	1.399 (9)	O1—C1	1.351 (9)
C3—C4	1.385 (11)	Cl1—C4	1.680 (7)
C4—C5	1.424 (7)	O1—H1	0.899
C5—C6	1.362 (8)	C3—H3	1.000
N7—N8	1.247 (12)	C5—H5	1.001
N7—C2	1.457 (12)	C6—H6	0.999
N8—C9	1.431 (12)	C10—H10	0.999
C9—C10	1.394 (8)	C11—H11	1.002
C9—C14	1.390 (6)	C12—H12	1.000
C10—C11	1.391 (10)	C13—H13	1.000
C11—C12	1.392 (6)	C14—H14	1.000
N8—N7—C2	121.0 (7)	C12—C13—C14	120.2 (4)
N7—N8—C9	120.1 (7)	C9—C14—C13	119.5 (5)
N7—C2—C1	125.6 (6)	C1—C6—H6	117.1
N7—C2—C3	114.8 (6)	C5—C6—H6	123.1
C1—C2—C3	119.7 (7)	C6—C5—H5	122.8
O1—C1—C2	118.3 (7)	C4—C5—H5	117.0
O1—C1—C6	121.9 (6)	C2—C3—H3	119.5
C2—C1—C6	119.9 (6)	C4—C3—H3	120.8
C1—C6—C5	119.8 (5)	C9—C10—H10	120.0
C6—C5—C4	120.0 (5)	C11—C10—H10	120.2
Cl1—C4—C5	118.0 (5)	C10—C11—H11	120.1
Cl1—C4—C3	121.1 (4)	C12—C11—H11	119.9
C5—C4—C3	120.9 (5)	C11—C12—H12	120.1
C2—C3—C4	119.7 (5)	C13—C12—H12	119.9
N8—C9—C10	115.7 (5)	C12—C13—H13	119.9
N8—C9—C14	123.7 (6)	C14—C13—H13	119.9
C10—C9—C14	120.5 (7)	C9—C14—H14	120.3
C9—C10—C11	119.8 (4)	C13—C14—H14	120.2
C10—C11—C12	120.0 (5)	C1—O1—H1	115.6
C11—C12—C13	120.0 (6)