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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018438/ya6064sup1.cif
Contains datablocks global, I

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S1600536801018438/ya6064Isup2.rtv
Contains datablock I

CCDC reference: 177200

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








Computing details top

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 top
Crystal data top
C12H9ClN2OZ = 4
Mr = 232.66F(000) = 480
Monoclinic, P21/nDx = 1.389 Mg m3
a = 12.384 (4) ÅCu Kα radiation, λ = 1.5418 Å
b = 19.767 (6) ÅT = 295 K
c = 4.554 (2) ÅParticle morphology: irregular blocks
β = 93.27 (3)°yellow
V = 1113.0 (7) Å3flat_sheet, 25 × 25 mm
Data collection top
DRON-3M
diffractometer (Burevestnik, Russia)
Data collection mode: reflection
Radiation source: X-ray sealed tubeScan method: step
Ni filtered monochromator2θmin = 7.8°, 2θmax = 70.0°, 2θstep = 0.02°
Specimen mounting: pressed as a thin layer in the specimen holder
Refinement top
Refinement on Inet115 parameters
Least-squares matrix: full with fixed elements per cycle10 restraints
Rp = 0.0320 constraints
Rwp = 0.042H-atom parameters not refined
Rexp = 0.025Weighting scheme based on measured s.u.'s
3151 data points(Δ/σ)max = 0.040
Excluded region(s): 7.00 - 7.78Background function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-VoigtPreferred orientation correction: Spherical harmonics (Ahtee et al., 1989)
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.3312 (8)0.3789 (3)0.3146 (19)0.091 (4)*
C20.2254 (7)0.3877 (5)0.199 (3)0.091 (4)*
C30.1426 (7)0.3466 (5)0.293 (2)0.091 (4)*
C40.1639 (8)0.2945 (5)0.494 (3)0.118 (4)*
C50.2681 (8)0.2839 (4)0.617 (3)0.118 (4)*
C60.3501 (7)0.3267 (4)0.524 (2)0.118 (4)*
N70.1933 (9)0.4382 (5)0.015 (3)0.091 (4)*
N80.2671 (9)0.4742 (5)0.095 (3)0.091 (4)*
C90.2380 (7)0.5246 (4)0.299 (2)0.091 (4)*
C100.3226 (7)0.5616 (6)0.416 (3)0.118 (4)*
C110.2985 (7)0.6110 (3)0.625 (2)0.118 (4)*
C120.1913 (6)0.6233 (5)0.715 (3)0.118 (4)*
C130.1074 (7)0.5883 (3)0.591 (2)0.118 (4)*
C140.1287 (7)0.5387 (6)0.383 (3)0.118 (4)*
O10.4146 (8)0.4169 (4)0.245 (3)0.091 (4)*
CL10.0600 (4)0.2456 (3)0.6133 (15)0.151 (5)
H10.40780.44910.1150.11*
H30.06590.35400.2130.11*
H50.28510.24810.7620.11*
H60.42590.31880.6070.11*
H100.39940.55000.3570.11*
H110.35790.63640.7150.11*
H120.17350.66050.8600.11*
H130.03050.59840.6600.11*
H140.07040.51140.3000.11*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
CL10.222 (8)0.139 (6)0.098 (9)0.002 (11)0.051 (12)0.051 (11)
Geometric parameters (Å, º) top
C1—C21.395 (14)C12—C131.394 (12)
C1—C61.415 (11)C13—C141.378 (15)
C2—C31.395 (13)O1—C11.330 (13)
C3—C41.393 (15)Cl1—C41.722 (12)
C4—C51.393 (15)C3—H31.008
C5—C61.405 (13)C5—H50.983
N7—C21.435 (17)C6—H61.004
N7—N81.230 (16)C10—H101.000
N8—C91.395 (15)C11—H110.998
C9—C101.407 (14)C12—H121.004
C9—C141.413 (13)C13—H131.006
C10—C111.384 (15)C14—H140.993
C11—C121.388 (12)O1—H10.870
O1—C1—C2124.4 (9)C12—C13—C14120.9 (8)
O1—C1—C6118.1 (9)C9—C14—C13118.0 (9)
C2—C1—C6117.4 (8)C1—C6—H6119.0
N7—C2—C1124.1 (9)C5—C6—H6118.0
N7—C2—C3115.7 (9)C6—C5—H5120.0
C1—C2—C3120.2 (10)C4—C5—H5122.0
C2—C3—C4121.2 (9)C2—C3—H3120.0
Cl1—C4—C5118.7 (9)C4—C3—H3119.0
Cl1—C4—C3120.4 (8)C9—C10—H10120.0
C5—C4—C3120.8 (9)C11—C10—H10121.0
C6—C5—C4117.2 (10)C10—C11—H11120.0
C1—C6—C5123.2 (9)C12—C11—H11120.0
N8—N7—C2115.0 (11)C11—C12—H12120.0
N7—N8—C9116.2 (11)C13—C12—H12119.0
N8—C9—C10117.0 (9)C12—C13—H13119.0
N8—C9—C14121.9 (9)C14—C13—H13120.0
C10—C9—C14121.2 (9)C9—C14—H14120.0
C9—C10—C11119.4 (8)C13—C14—H14122.0
C10—C11—C12119.4 (8)C1—O1—H1122.0
C11—C12—C13121.0 (10)
 

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