organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018438/ya6064sup1.cif | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S1600536801018438/ya6064Isup2.rtv |
CCDC reference: 177200
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
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) Å3 | flat_sheet, 25 × 25 mm |
Data collection top
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 top
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 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
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
CL1 | 0.222 (8) | 0.139 (6) | 0.098 (9) | −0.002 (11) | 0.051 (12) | −0.051 (11) |
Geometric parameters (Å, º) top
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) |