2,6-Di­methyl-4-(4-chloro­phenyl­diazenyl)­phenol

The crystal structure of the title compound, C₁₄H₁₃ClN₂O, determined at 213 K, shows that the mol­ecule is approx­imately planar in the solid state, having a trans configuration with respect to the azo double bond, as found for other diazene (azo­benzene) derivatives. The dihedral angle between the planes of the two aromatic rings is 5.48 (10)°. Hydro­xyl groups are linked to each other by intermolecular hydrogen bonds along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.109
• Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,6-dimethyl-4-(4-chlorophenyldiazenyl)phenol

Crystal data

C14H13ClN2O	F(000) = 544
Mr = 260.71	Dx = 1.384 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.618 (3) Å	Cell parameters from 75351.88 reflections
b = 3.9575 (8) Å	θ = 1.9–29.3°
c = 21.643 (4) Å	µ = 0.29 mm^−1
β = 91.887 (3)°	T = 213 K
V = 1251.4 (4) Å^3	Prism, orange
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection

Bruker AXS SMART CCD Diffractometer	2206 independent reflections
Radiation source: fine-focus sealed tube	1790 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω Scans scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan SADABS; Bruker, 1998	h = −17→15
Tmin = 0.944, Tmax = 0.971	k = −4→3
5900 measured reflections	l = −23→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0665P)^2 + 0.2052P] where P = (Fo^2 + 2Fc^2)/3
2206 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.43476 (3)	0.65350 (14)	0.30896 (2)	0.0438 (2)
O1	0.99702 (9)	−0.1446 (4)	0.70499 (6)	0.0334 (3)
N1	0.74583 (11)	0.2764 (4)	0.47780 (7)	0.0359 (4)
N2	0.72467 (11)	0.1303 (4)	0.52681 (7)	0.0373 (4)
C1	0.66805 (13)	0.3505 (5)	0.43831 (8)	0.0329 (4)
C2	0.68494 (13)	0.5115 (6)	0.38299 (9)	0.0416 (5)
C3	0.61389 (14)	0.5996 (6)	0.34222 (10)	0.0417 (5)
C4	0.52536 (13)	0.5280 (5)	0.35816 (9)	0.0336 (5)
C5	0.50688 (14)	0.3636 (6)	0.41249 (9)	0.0400 (5)
C6	0.57840 (13)	0.2749 (6)	0.45249 (9)	0.0384 (5)
C7	0.79866 (12)	0.0612 (5)	0.56932 (8)	0.0320 (4)
C8	0.77397 (13)	−0.0980 (5)	0.62332 (9)	0.0338 (5)
C9	0.83822 (12)	−0.1715 (5)	0.67022 (8)	0.0305 (4)
C10	0.92888 (12)	−0.0839 (5)	0.66033 (8)	0.0280 (4)
C11	0.95630 (12)	0.0782 (5)	0.60644 (8)	0.0290 (4)
C12	0.89004 (13)	0.1496 (5)	0.56112 (9)	0.0331 (4)
C13	0.80980 (15)	−0.3297 (6)	0.72995 (10)	0.0388 (5)
C14	1.05496 (14)	0.1771 (6)	0.59939 (10)	0.0372 (5)
H1O	0.9818 (16)	−0.288 (6)	0.7262 (11)	0.045 (7)*
H2	0.7442 (16)	0.561 (6)	0.3738 (10)	0.054 (7)*
H3	0.6236 (15)	0.729 (5)	0.3029 (11)	0.049 (6)*
H5	0.4468 (16)	0.312 (5)	0.4231 (10)	0.047 (6)*
H6	0.5703 (16)	0.161 (6)	0.4911 (12)	0.057 (7)*
H8	0.7133 (16)	−0.159 (5)	0.6268 (9)	0.042 (6)*
H12	0.9081 (15)	0.275 (5)	0.5223 (10)	0.046 (6)*
H13A	0.843 (2)	−0.530 (9)	0.7394 (13)	0.086 (9)*
H13B	0.822 (2)	−0.189 (7)	0.7639 (13)	0.082 (9)*
H13C	0.7500 (18)	−0.382 (6)	0.7283 (10)	0.052 (7)*
H14A	1.0947 (16)	−0.012 (7)	0.6040 (10)	0.058 (7)*
H14B	1.0761 (15)	0.344 (5)	0.6294 (9)	0.044 (6)*
H14C	1.0665 (17)	0.285 (6)	0.5591 (11)	0.057 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0339 (3)	0.0560 (4)	0.0407 (3)	0.0028 (2)	−0.0123 (2)	0.0040 (2)
O1	0.0270 (7)	0.0425 (9)	0.0304 (7)	−0.0019 (6)	−0.0066 (5)	0.0034 (7)
N1	0.0310 (8)	0.0454 (10)	0.0309 (8)	0.0003 (7)	−0.0048 (7)	0.0011 (8)
N2	0.0314 (9)	0.0475 (11)	0.0325 (9)	−0.0004 (7)	−0.0066 (7)	0.0013 (8)
C1	0.0302 (10)	0.0390 (11)	0.0291 (10)	0.0003 (8)	−0.0041 (8)	−0.0002 (8)
C2	0.0264 (10)	0.0603 (14)	0.0379 (12)	−0.0033 (10)	−0.0003 (8)	0.0089 (10)
C3	0.0334 (10)	0.0573 (14)	0.0342 (11)	−0.0019 (10)	−0.0028 (8)	0.0089 (10)
C4	0.0300 (9)	0.0394 (11)	0.0309 (10)	0.0008 (8)	−0.0069 (7)	−0.0016 (9)
C5	0.0270 (10)	0.0541 (14)	0.0386 (11)	−0.0054 (9)	−0.0031 (8)	0.0028 (10)
C6	0.0337 (10)	0.0505 (13)	0.0308 (10)	−0.0057 (9)	−0.0015 (8)	0.0054 (9)
C7	0.0279 (9)	0.0393 (11)	0.0285 (9)	0.0014 (8)	−0.0050 (7)	−0.0036 (8)
C8	0.0231 (9)	0.0454 (12)	0.0329 (10)	−0.0020 (8)	−0.0019 (7)	−0.0031 (9)
C9	0.0283 (9)	0.0357 (11)	0.0273 (9)	0.0002 (8)	−0.0014 (7)	−0.0034 (8)
C10	0.0261 (9)	0.0311 (10)	0.0265 (9)	0.0017 (7)	−0.0042 (7)	−0.0066 (8)
C11	0.0276 (9)	0.0310 (10)	0.0283 (9)	0.0003 (7)	−0.0006 (7)	−0.0045 (8)
C12	0.0336 (10)	0.0370 (11)	0.0286 (9)	−0.0017 (8)	−0.0012 (8)	−0.0011 (9)
C13	0.0292 (11)	0.0547 (15)	0.0324 (11)	−0.0032 (10)	−0.0004 (8)	0.0043 (10)
C14	0.0295 (10)	0.0444 (13)	0.0377 (11)	−0.0047 (9)	0.0000 (8)	0.0009 (10)

Geometric parameters (Å, º)

Cl1—C4	1.7437 (19)	C7—C8	1.386 (3)
O1—C10	1.386 (2)	C7—C12	1.397 (3)
O1—H1O	0.77 (2)	C8—C9	1.391 (3)
N1—N2	1.256 (2)	C8—H8	0.93 (2)
N1—C1	1.430 (2)	C9—C10	1.393 (3)
N2—C7	1.424 (2)	C9—C13	1.507 (3)
C1—C2	1.385 (3)	C10—C11	1.401 (3)
C1—C6	1.388 (3)	C11—C12	1.385 (2)
C2—C3	1.385 (3)	C11—C14	1.507 (3)
C2—H2	0.92 (2)	C12—H12	1.01 (2)
C3—C4	1.379 (3)	C13—H13A	0.96 (3)
C3—H3	1.00 (2)	C13—H13B	0.94 (3)
C4—C5	1.379 (3)	C13—H13C	0.90 (3)
C5—C6	1.380 (3)	C14—H14A	0.95 (3)
C5—H5	0.93 (2)	C14—H14B	0.97 (2)
C6—H6	0.96 (2)	C14—H14C	0.99 (2)
C10—O1—H1O	109.3 (17)	C9—C8—H8	120.6 (13)
N2—N1—C1	112.73 (15)	C8—C9—C10	117.28 (17)
N1—N2—C7	115.56 (15)	C8—C9—C13	120.95 (17)
C2—C1—C6	119.12 (17)	C10—C9—C13	121.74 (16)
C2—C1—N1	116.74 (16)	O1—C10—C9	121.00 (16)
C6—C1—N1	124.14 (17)	O1—C10—C11	116.17 (15)
C1—C2—C3	120.96 (18)	C9—C10—C11	122.80 (16)
C1—C2—H2	118.9 (14)	C12—C11—C10	118.06 (16)
C3—C2—H2	120.2 (14)	C12—C11—C14	121.65 (18)
C4—C3—C2	118.66 (19)	C10—C11—C14	120.28 (16)
C4—C3—H3	118.6 (13)	C11—C12—C7	120.53 (18)
C2—C3—H3	122.6 (13)	C11—C12—H12	119.2 (12)
C5—C4—C3	121.44 (18)	C7—C12—H12	120.2 (12)
C5—C4—Cl1	119.25 (15)	C9—C13—H13A	112.2 (17)
C3—C4—Cl1	119.30 (16)	C9—C13—H13B	112.0 (17)
C4—C5—C6	119.29 (18)	H13A—C13—H13B	104 (2)
C4—C5—H5	121.5 (13)	C9—C13—H13C	111.3 (15)
C6—C5—H5	119.2 (13)	H13A—C13—H13C	108 (2)
C5—C6—C1	120.50 (19)	H13B—C13—H13C	109 (2)
C5—C6—H6	123.3 (15)	C11—C14—H14A	111.7 (15)
C1—C6—H6	116.2 (15)	C11—C14—H14B	113.1 (13)
C8—C7—C12	119.84 (17)	H14A—C14—H14B	106.6 (19)
C8—C7—N2	114.75 (16)	C11—C14—H14C	113.3 (14)
C12—C7—N2	125.37 (17)	H14A—C14—H14C	108 (2)
C7—C8—C9	121.48 (17)	H14B—C14—H14C	103.7 (18)
C7—C8—H8	118.0 (13)
C1—N1—N2—C7	−177.66 (16)	N2—C7—C8—C9	−177.74 (18)
N2—N1—C1—C2	−179.88 (18)	C7—C8—C9—C10	−1.1 (3)
N2—N1—C1—C6	1.0 (3)	C7—C8—C9—C13	177.11 (19)
C6—C1—C2—C3	0.5 (3)	C8—C9—C10—O1	179.23 (16)
N1—C1—C2—C3	−178.7 (2)	C13—C9—C10—O1	1.1 (3)
C1—C2—C3—C4	0.8 (3)	C8—C9—C10—C11	1.3 (3)
C2—C3—C4—C5	−1.8 (3)	C13—C9—C10—C11	−176.85 (19)
C2—C3—C4—Cl1	177.25 (17)	O1—C10—C11—C12	−178.77 (16)
C3—C4—C5—C6	1.3 (3)	C9—C10—C11—C12	−0.8 (3)
Cl1—C4—C5—C6	−177.71 (17)	O1—C10—C11—C14	−0.1 (3)
C4—C5—C6—C1	0.1 (3)	C9—C10—C11—C14	177.89 (19)
C2—C1—C6—C5	−1.0 (3)	C10—C11—C12—C7	−0.1 (3)
N1—C1—C6—C5	178.15 (19)	C14—C11—C12—C7	−178.70 (18)
N1—N2—C7—C8	179.53 (17)	C8—C7—C12—C11	0.3 (3)
N1—N2—C7—C12	1.6 (3)	N2—C7—C12—C11	178.12 (18)
C12—C7—C8—C9	0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1^i	0.77 (2)	2.06 (2)	2.7762 (19)	154 (2)

Symmetry code: (i) −x+2, y−1/2, −z+3/2.