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In the title structure, C14H11N2O2Cl, the benzene rings are in a trans configuration with respect to the azo double bond and the mol­ecule is essentially planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025110/lh6475sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025110/lh6475Isup2.hkl
Contains datablock I

CCDC reference: 283948

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.038
  • wR factor = 0.111
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Acetyl-4-(2-chorophenyldiazenyl)phenol top
Crystal data top
C14H11ClN2O2F(000) = 1136
Mr = 274.70Dx = 1.422 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8416 reflections
a = 10.8170 (9) Åθ = 1.6–28.0°
b = 9.3912 (6) ŵ = 0.30 mm1
c = 25.3745 (18) ÅT = 296 K
β = 95.576 (6)°Plate, brown
V = 2565.5 (3) Å30.40 × 0.29 × 0.11 mm
Z = 8
Data collection top
Stoe IPDS-2
diffractometer
3074 independent reflections
Radiation source: fine-focus sealed tube1746 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 6.67 pixels mm-1θmax = 28.0°, θmin = 1.6°
rotation method scansh = 1414
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1212
Tmin = 0.888, Tmax = 0.972l = 3333
10193 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0615P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max = 0.001
3074 reflectionsΔρmax = 0.17 e Å3
193 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0024 (6)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.46673 (14)0.22707 (18)0.57493 (6)0.0537 (4)
C20.52533 (16)0.34948 (19)0.55978 (7)0.0627 (4)
C30.59144 (18)0.4342 (2)0.59657 (8)0.0722 (5)
H30.63090.51570.58580.087*
C40.59918 (18)0.3980 (2)0.64964 (8)0.0730 (5)
C50.54172 (17)0.2787 (3)0.66546 (7)0.0714 (5)
C60.47552 (15)0.1927 (2)0.62861 (6)0.0623 (4)
C70.32897 (14)0.07282 (17)0.45617 (6)0.0526 (4)
C80.26315 (16)0.04580 (18)0.47133 (7)0.0604 (4)
C90.19491 (17)0.1257 (2)0.43421 (7)0.0636 (4)
C100.19019 (15)0.09083 (18)0.38082 (6)0.0566 (4)
C110.25683 (15)0.02657 (16)0.36469 (6)0.0534 (4)
C120.32639 (15)0.10669 (17)0.40338 (6)0.0553 (4)
H120.37180.18440.39320.066*
C130.25318 (19)0.06168 (19)0.30795 (7)0.0665 (5)
C140.3257 (2)0.1834 (2)0.28979 (8)0.0935 (7)
H14A0.31330.19000.25190.140*
H14B0.41230.16910.30060.140*
H14C0.29840.27000.30510.140*
Cl10.40438 (5)0.04053 (7)0.64961 (2)0.0948 (2)
N10.39525 (12)0.13467 (15)0.53939 (5)0.0575 (3)
N20.40115 (12)0.16376 (15)0.49173 (5)0.0581 (3)
O10.11948 (12)0.17174 (13)0.34646 (5)0.0764 (4)
H1O0.12390.14210.31630.115*
O20.18929 (15)0.00969 (16)0.27527 (5)0.0900 (4)
H20.5201 (17)0.371 (2)0.5239 (8)0.077 (6)*
H40.637 (2)0.459 (2)0.6726 (10)0.101 (7)*
H50.5465 (18)0.253 (2)0.7024 (9)0.092 (6)*
H80.2654 (16)0.0689 (19)0.5086 (8)0.075 (5)*
H90.1511 (17)0.208 (2)0.4445 (7)0.075 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0492 (8)0.0658 (10)0.0453 (8)0.0045 (8)0.0003 (6)0.0060 (7)
C20.0705 (10)0.0674 (11)0.0493 (9)0.0012 (9)0.0013 (8)0.0039 (8)
C30.0791 (12)0.0680 (11)0.0684 (12)0.0041 (10)0.0014 (9)0.0124 (9)
C40.0697 (11)0.0872 (14)0.0598 (11)0.0011 (11)0.0049 (9)0.0222 (11)
C50.0611 (10)0.1065 (16)0.0454 (9)0.0016 (10)0.0012 (8)0.0086 (10)
C60.0528 (9)0.0872 (12)0.0465 (9)0.0017 (9)0.0022 (7)0.0003 (8)
C70.0571 (9)0.0559 (9)0.0440 (8)0.0032 (7)0.0005 (7)0.0032 (7)
C80.0669 (10)0.0651 (10)0.0488 (9)0.0010 (8)0.0036 (8)0.0040 (8)
C90.0723 (11)0.0598 (10)0.0586 (10)0.0095 (9)0.0055 (8)0.0010 (8)
C100.0614 (9)0.0538 (9)0.0537 (9)0.0001 (8)0.0003 (7)0.0079 (7)
C110.0640 (9)0.0505 (8)0.0447 (8)0.0039 (7)0.0004 (7)0.0038 (7)
C120.0667 (10)0.0509 (8)0.0474 (8)0.0021 (8)0.0009 (7)0.0015 (7)
C130.0898 (12)0.0620 (10)0.0459 (8)0.0015 (9)0.0031 (8)0.0042 (8)
C140.139 (2)0.0876 (14)0.0517 (10)0.0249 (14)0.0014 (11)0.0149 (10)
Cl10.0905 (4)0.1294 (5)0.0630 (3)0.0321 (3)0.0004 (2)0.0236 (3)
N10.0599 (8)0.0682 (9)0.0433 (7)0.0024 (7)0.0006 (6)0.0023 (6)
N20.0638 (8)0.0653 (8)0.0441 (7)0.0016 (7)0.0004 (6)0.0038 (6)
O10.0934 (9)0.0686 (8)0.0648 (8)0.0185 (7)0.0046 (7)0.0130 (6)
O20.1300 (12)0.0894 (9)0.0472 (7)0.0201 (9)0.0089 (7)0.0091 (7)
Geometric parameters (Å, º) top
C1—C21.385 (2)C8—H80.968 (19)
C1—C61.394 (2)C9—C101.390 (2)
C1—N11.424 (2)C9—H90.959 (19)
C2—C31.373 (2)C10—O11.3391 (19)
C2—H20.93 (2)C10—C111.400 (2)
C3—C41.383 (3)C11—C121.397 (2)
C3—H30.9300C11—C131.474 (2)
C4—C51.361 (3)C12—H120.9300
C4—H40.89 (2)C13—O21.226 (2)
C5—C61.382 (3)C13—C141.485 (3)
C5—H50.96 (2)C14—H14A0.9600
C6—Cl11.7317 (19)C14—H14B0.9600
C7—C121.375 (2)C14—H14C0.9600
C7—C81.396 (2)N1—N21.2475 (18)
C7—N21.420 (2)O1—H1O0.8200
C8—C91.364 (2)
C2—C1—C6118.27 (16)C8—C9—C10120.62 (16)
C2—C1—N1124.39 (14)C8—C9—H9120.4 (11)
C6—C1—N1117.32 (15)C10—C9—H9118.9 (11)
C3—C2—C1120.94 (17)O1—C10—C9117.73 (15)
C3—C2—H2121.3 (12)O1—C10—C11122.29 (14)
C1—C2—H2117.7 (12)C9—C10—C11119.97 (15)
C2—C3—C4119.87 (19)C12—C11—C10118.42 (14)
C2—C3—H3120.1C12—C11—C13121.83 (15)
C4—C3—H3120.1C10—C11—C13119.75 (14)
C5—C4—C3120.20 (19)C7—C12—C11121.25 (15)
C5—C4—H4122.1 (15)C7—C12—H12119.4
C3—C4—H4117.5 (15)C11—C12—H12119.4
C4—C5—C6120.21 (18)O2—C13—C11119.89 (16)
C4—C5—H5120.9 (13)O2—C13—C14119.41 (16)
C6—C5—H5118.9 (13)C11—C13—C14120.70 (16)
C5—C6—C1120.51 (18)C13—C14—H14A109.5
C5—C6—Cl1119.38 (14)C13—C14—H14B109.5
C1—C6—Cl1120.10 (14)H14A—C14—H14B109.5
C12—C7—C8119.38 (15)C13—C14—H14C109.5
C12—C7—N2115.97 (14)H14A—C14—H14C109.5
C8—C7—N2124.65 (14)H14B—C14—H14C109.5
C9—C8—C7120.35 (16)N2—N1—C1113.87 (13)
C9—C8—H8120.8 (11)N1—N2—C7114.05 (14)
C7—C8—H8118.9 (11)C10—O1—H1O109.5
C6—C1—C2—C30.6 (2)C9—C10—C11—C120.4 (2)
N1—C1—C2—C3179.18 (15)O1—C10—C11—C131.8 (2)
C1—C2—C3—C40.5 (3)C9—C10—C11—C13178.97 (16)
C2—C3—C4—C50.1 (3)C8—C7—C12—C111.5 (2)
C3—C4—C5—C60.1 (3)N2—C7—C12—C11178.87 (14)
C4—C5—C6—C10.0 (3)C10—C11—C12—C70.7 (2)
C4—C5—C6—Cl1179.41 (14)C13—C11—C12—C7179.98 (16)
C2—C1—C6—C50.4 (2)C12—C11—C13—O2178.72 (16)
N1—C1—C6—C5179.00 (15)C10—C11—C13—O21.9 (3)
C2—C1—C6—Cl1179.79 (13)C12—C11—C13—C141.0 (3)
N1—C1—C6—Cl11.6 (2)C10—C11—C13—C14178.41 (17)
C12—C7—C8—C91.3 (3)C2—C1—N1—N28.0 (2)
N2—C7—C8—C9179.11 (15)C6—C1—N1—N2173.44 (15)
C7—C8—C9—C100.2 (3)C1—N1—N2—C7179.37 (12)
C8—C9—C10—O1178.63 (16)C12—C7—N2—N1175.96 (14)
C8—C9—C10—C110.6 (3)C8—C7—N2—N14.4 (2)
O1—C10—C11—C12178.79 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O20.821.812.5327 (19)146
 

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