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

The high-temperature form of the title compound, C₁₂H₉ClN₂O, (I), was obtained from the melt. The mol­ecule of (I) is almost planar; the dihedral angle formed by the planes of the phenyl rings is 8.0 (5)°. Translationally related mol­ecules form stacks with an interplanar separation of 3.41 (1) Å.

Key indicators

• Powder X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.000
• wR factor = 0.000
• Data-to-parameter ratio = 0.0

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	Z = 4
Mr = 232.66	F(000) = 480
Monoclinic, P21/n	Dx = 1.389 Mg m^−3
a = 12.384 (4) Å	Cu Kα radiation, λ = 1.5418 Å
b = 19.767 (6) Å	T = 295 K
c = 4.554 (2) Å	Particle morphology: irregular blocks
β = 93.27 (3)°	yellow
V = 1113.0 (7) Å^3	flat_sheet, 25 × 25 mm

Data collection

DRON-3M diffractometer (Burevestnik, Russia)	Data collection mode: reflection
Radiation source: X-ray sealed tube	Scan method: step
Ni filtered monochromator	2θmin = 7.8°, 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 = 0.032	0 constraints
Rwp = 0.042	H-atom parameters not refined
Rexp = 0.025	Weighting scheme based on measured s.u.'s
3151 data points	(Δ/σ)max = 0.040
Excluded region(s): 7.00 - 7.78	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	0.3312 (8)	0.3789 (3)	0.3146 (19)	0.091 (4)*
C2	0.2254 (7)	0.3877 (5)	0.199 (3)	0.091 (4)*
C3	0.1426 (7)	0.3466 (5)	0.293 (2)	0.091 (4)*
C4	0.1639 (8)	0.2945 (5)	0.494 (3)	0.118 (4)*
C5	0.2681 (8)	0.2839 (4)	0.617 (3)	0.118 (4)*
C6	0.3501 (7)	0.3267 (4)	0.524 (2)	0.118 (4)*
N7	0.1933 (9)	0.4382 (5)	−0.015 (3)	0.091 (4)*
N8	0.2671 (9)	0.4742 (5)	−0.095 (3)	0.091 (4)*
C9	0.2380 (7)	0.5246 (4)	−0.299 (2)	0.091 (4)*
C10	0.3226 (7)	0.5616 (6)	−0.416 (3)	0.118 (4)*
C11	0.2985 (7)	0.6110 (3)	−0.625 (2)	0.118 (4)*
C12	0.1913 (6)	0.6233 (5)	−0.715 (3)	0.118 (4)*
C13	0.1074 (7)	0.5883 (3)	−0.591 (2)	0.118 (4)*
C14	0.1287 (7)	0.5387 (6)	−0.383 (3)	0.118 (4)*
O1	0.4146 (8)	0.4169 (4)	0.245 (3)	0.091 (4)*
CL1	0.0600 (4)	0.2456 (3)	0.6133 (15)	0.151 (5)
H1	0.4078	0.4491	0.115	0.11*
H3	0.0659	0.3540	0.213	0.11*
H5	0.2851	0.2481	0.762	0.11*
H6	0.4259	0.3188	0.607	0.11*
H10	0.3994	0.5500	−0.357	0.11*
H11	0.3579	0.6364	−0.715	0.11*
H12	0.1735	0.6605	−0.860	0.11*
H13	0.0305	0.5984	−0.660	0.11*
H14	0.0704	0.5114	−0.300	0.11*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
CL1	0.222 (8)	0.139 (6)	0.098 (9)	−0.002 (11)	0.051 (12)	−0.051 (11)

Geometric parameters (Å, º)

C1—C2	1.395 (14)	C12—C13	1.394 (12)
C1—C6	1.415 (11)	C13—C14	1.378 (15)
C2—C3	1.395 (13)	O1—C1	1.330 (13)
C3—C4	1.393 (15)	Cl1—C4	1.722 (12)
C4—C5	1.393 (15)	C3—H3	1.008
C5—C6	1.405 (13)	C5—H5	0.983
N7—C2	1.435 (17)	C6—H6	1.004
N7—N8	1.230 (16)	C10—H10	1.000
N8—C9	1.395 (15)	C11—H11	0.998
C9—C10	1.407 (14)	C12—H12	1.004
C9—C14	1.413 (13)	C13—H13	1.006
C10—C11	1.384 (15)	C14—H14	0.993
C11—C12	1.388 (12)	O1—H1	0.870
O1—C1—C2	124.4 (9)	C12—C13—C14	120.9 (8)
O1—C1—C6	118.1 (9)	C9—C14—C13	118.0 (9)
C2—C1—C6	117.4 (8)	C1—C6—H6	119.0
N7—C2—C1	124.1 (9)	C5—C6—H6	118.0
N7—C2—C3	115.7 (9)	C6—C5—H5	120.0
C1—C2—C3	120.2 (10)	C4—C5—H5	122.0
C2—C3—C4	121.2 (9)	C2—C3—H3	120.0
Cl1—C4—C5	118.7 (9)	C4—C3—H3	119.0
Cl1—C4—C3	120.4 (8)	C9—C10—H10	120.0
C5—C4—C3	120.8 (9)	C11—C10—H10	121.0
C6—C5—C4	117.2 (10)	C10—C11—H11	120.0
C1—C6—C5	123.2 (9)	C12—C11—H11	120.0
N8—N7—C2	115.0 (11)	C11—C12—H12	120.0
N7—N8—C9	116.2 (11)	C13—C12—H12	119.0
N8—C9—C10	117.0 (9)	C12—C13—H13	119.0
N8—C9—C14	121.9 (9)	C14—C13—H13	120.0
C10—C9—C14	121.2 (9)	C9—C14—H14	120.0
C9—C10—C11	119.4 (8)	C13—C14—H14	122.0
C10—C11—C12	119.4 (8)	C1—O1—H1	122.0
C11—C12—C13	121.0 (10)