(E)-2-Acetyl-4-(phenyl­diazen­yl)phenol

The mol­ecule of the title compound, C₁₄H₁₂N₂O₂, is nearly planar and displays a trans configuration with respect to the N=N double bond, as found for other diazene derivatives. There is an intra­molecular O—H...O hydrogen bond and the crystal packing is governed by π–π stacking.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.181
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   N2      ..       9.98 su

Alert level C
DIFMN02_ALERT_2_C  The minimum difference density is < -0.1*ZMAX*0.75
            _refine_diff_density_min given =     -0.617
            Test value =     -0.600
DIFMN03_ALERT_1_C  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............      -0.62 e/A   
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C8      ..       3.00 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 5 Informative message, check

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Computing details

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: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-2-Acetyl-4-(phenyldiazenyl)phenol

Crystal data

C14H12N2O2	F(000) = 504
Mr = 240.26	Dx = 1.313 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14816 reflections
a = 8.8115 (7) Å	θ = 2.4–27.9°
b = 10.2794 (6) Å	µ = 0.09 mm^−1
c = 14.2035 (13) Å	T = 293 K
β = 109.143 (6)°	Prism, brown
V = 1215.37 (16) Å^3	0.46 × 0.29 × 0.20 mm
Z = 4

Data collection

Stoe IPDS 2 diffractometer	2394 independent reflections
Radiation source: fine-focus sealed tube	1387 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.971, Tmax = 0.983	l = −17→17
17183 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.11P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
2394 reflections	Δρmax = 0.56 e Å^−3
152 parameters	Δρmin = −0.62 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.116 (13)

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
C1	0.8033 (4)	0.5345 (3)	0.3864 (2)	0.0855 (9)
H1A	0.8338	0.5575	0.4557	0.128*
H1B	0.8205	0.4432	0.3803	0.128*
H1C	0.6917	0.5544	0.3544	0.128*
C2	0.9019 (3)	0.6097 (3)	0.33829 (18)	0.0683 (7)
C3	0.8785 (3)	0.5928 (2)	0.23122 (16)	0.0554 (6)
C4	0.9706 (3)	0.6654 (2)	0.18611 (18)	0.0620 (6)
C5	0.9493 (3)	0.6482 (2)	0.08522 (19)	0.0676 (7)
H5	1.0082	0.6982	0.0549	0.081*
C6	0.8423 (3)	0.5583 (3)	0.03073 (17)	0.0645 (7)
H6	0.8297	0.5469	−0.0364	0.077*
C7	0.7516 (3)	0.4835 (2)	0.07459 (16)	0.0597 (4)
C8	0.7689 (3)	0.5038 (2)	0.17323 (17)	0.0557 (6)
H8	0.7053	0.4567	0.2019	0.067*
C9	0.5300 (3)	0.2613 (2)	−0.11108 (19)	0.0642 (5)
C10	0.5166 (3)	0.2435 (3)	−0.20934 (19)	0.0705 (7)
H10	0.5768	0.2950	−0.2377	0.085*
C11	0.4164 (3)	0.1512 (3)	−0.2658 (2)	0.0766 (8)
H11	0.4087	0.1399	−0.3322	0.092*
C12	0.3273 (4)	0.0755 (3)	−0.2248 (2)	0.0782 (8)
H12	0.2574	0.0137	−0.2637	0.094*
C13	0.3406 (4)	0.0900 (3)	−0.1264 (2)	0.0872 (9)
H13	0.2811	0.0368	−0.0986	0.105*
C14	0.4416 (4)	0.1833 (3)	−0.0683 (2)	0.0770 (8)
H14	0.4503	0.1937	−0.0016	0.092*
N1	0.6402 (2)	0.38181 (19)	0.02568 (14)	0.0597 (4)
N2	0.6381 (2)	0.36316 (19)	−0.06080 (15)	0.0642 (5)
O1	1.0811 (3)	0.7520 (2)	0.23672 (15)	0.0936 (7)
H1	1.0829	0.7548	0.2948	0.140*
O2	1.0043 (3)	0.6867 (2)	0.38831 (15)	0.0987 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.095 (2)	0.109 (2)	0.0587 (15)	−0.0117 (18)	0.0335 (15)	−0.0037 (15)
C2	0.0711 (16)	0.0771 (17)	0.0561 (14)	−0.0019 (14)	0.0200 (13)	−0.0087 (12)
C3	0.0602 (14)	0.0558 (13)	0.0502 (12)	0.0014 (11)	0.0179 (11)	−0.0026 (10)
C4	0.0658 (15)	0.0593 (14)	0.0634 (14)	−0.0057 (12)	0.0246 (12)	−0.0116 (11)
C5	0.0787 (17)	0.0674 (15)	0.0644 (15)	−0.0055 (13)	0.0342 (14)	−0.0043 (12)
C6	0.0742 (16)	0.0711 (15)	0.0479 (12)	0.0105 (13)	0.0197 (12)	−0.0020 (11)
C7	0.0622 (9)	0.0631 (9)	0.0501 (8)	0.0076 (7)	0.0135 (7)	−0.0047 (6)
C8	0.0593 (14)	0.0518 (12)	0.0555 (13)	0.0029 (10)	0.0183 (11)	0.0004 (10)
C9	0.0625 (10)	0.0629 (9)	0.0638 (10)	0.0046 (7)	0.0162 (8)	−0.0062 (7)
C10	0.0718 (16)	0.0718 (16)	0.0670 (16)	0.0010 (13)	0.0216 (14)	−0.0056 (12)
C11	0.0745 (17)	0.0845 (18)	0.0678 (16)	−0.0012 (15)	0.0195 (14)	−0.0176 (14)
C12	0.0747 (17)	0.0742 (18)	0.0827 (19)	−0.0056 (14)	0.0218 (15)	−0.0258 (14)
C13	0.095 (2)	0.083 (2)	0.092 (2)	−0.0237 (16)	0.0419 (18)	−0.0197 (16)
C14	0.0879 (19)	0.0809 (18)	0.0648 (16)	−0.0026 (15)	0.0288 (15)	−0.0155 (13)
N1	0.0622 (9)	0.0631 (9)	0.0501 (8)	0.0076 (7)	0.0135 (7)	−0.0047 (6)
N2	0.0625 (10)	0.0629 (9)	0.0638 (10)	0.0046 (7)	0.0162 (8)	−0.0062 (7)
O1	0.1071 (15)	0.0977 (15)	0.0860 (13)	−0.0442 (12)	0.0454 (12)	−0.0321 (11)
O2	0.1061 (15)	0.1254 (18)	0.0659 (12)	−0.0378 (14)	0.0299 (12)	−0.0356 (12)

Geometric parameters (Å, º)

C1—C2	1.487 (4)	C8—H8	0.9300
C1—H1A	0.9600	C9—C10	1.374 (4)
C1—H1B	0.9600	C9—C14	1.389 (4)
C1—H1C	0.9600	C9—N2	1.438 (3)
C2—O2	1.235 (3)	C10—C11	1.363 (4)
C2—C3	1.476 (3)	C10—H10	0.9300
C3—C8	1.387 (3)	C11—C12	1.364 (4)
C3—C4	1.403 (3)	C11—H11	0.9300
C4—O1	1.341 (3)	C12—C13	1.372 (4)
C4—C5	1.394 (3)	C12—H12	0.9300
C5—C6	1.365 (4)	C13—C14	1.383 (4)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.395 (4)	C14—H14	0.9300
C6—H6	0.9300	N1—N2	1.237 (3)
C7—C8	1.375 (3)	O1—H1	0.8200
C7—N1	1.446 (3)
C2—C1—H1A	109.5	C7—C8—C3	121.9 (2)
C2—C1—H1B	109.5	C7—C8—H8	119.0
H1A—C1—H1B	109.5	C3—C8—H8	119.0
C2—C1—H1C	109.5	C10—C9—C14	119.6 (3)
H1A—C1—H1C	109.5	C10—C9—N2	115.1 (2)
H1B—C1—H1C	109.5	C14—C9—N2	125.3 (2)
O2—C2—C3	119.8 (2)	C11—C10—C9	120.9 (3)
O2—C2—C1	119.7 (2)	C11—C10—H10	119.5
C3—C2—C1	120.5 (2)	C9—C10—H10	119.5
C8—C3—C4	118.3 (2)	C10—C11—C12	119.9 (3)
C8—C3—C2	121.6 (2)	C10—C11—H11	120.1
C4—C3—C2	120.1 (2)	C12—C11—H11	120.1
O1—C4—C5	117.7 (2)	C11—C12—C13	120.3 (3)
O1—C4—C3	122.4 (2)	C11—C12—H12	119.9
C5—C4—C3	119.9 (2)	C13—C12—H12	119.9
C6—C5—C4	120.2 (2)	C12—C13—C14	120.5 (3)
C6—C5—H5	119.9	C12—C13—H13	119.8
C4—C5—H5	119.9	C14—C13—H13	119.8
C5—C6—C7	120.7 (2)	C13—C14—C9	118.8 (3)
C5—C6—H6	119.6	C13—C14—H14	120.6
C7—C6—H6	119.6	C9—C14—H14	120.6
C8—C7—C6	118.9 (2)	N2—N1—C7	112.1 (2)
C8—C7—N1	115.5 (2)	N1—N2—C9	113.5 (2)
C6—C7—N1	125.6 (2)	C4—O1—H1	109.5
O2—C2—C3—C8	177.6 (2)	C4—C3—C8—C7	1.5 (3)
C1—C2—C3—C8	−2.3 (4)	C2—C3—C8—C7	−177.1 (2)
O2—C2—C3—C4	−0.9 (4)	C14—C9—C10—C11	0.8 (4)
C1—C2—C3—C4	179.2 (2)	N2—C9—C10—C11	−179.1 (2)
C8—C3—C4—O1	−179.0 (2)	C9—C10—C11—C12	0.2 (4)
C2—C3—C4—O1	−0.4 (4)	C10—C11—C12—C13	−1.3 (4)
C8—C3—C4—C5	0.8 (3)	C11—C12—C13—C14	1.3 (5)
C2—C3—C4—C5	179.4 (2)	C12—C13—C14—C9	−0.3 (4)
O1—C4—C5—C6	177.9 (2)	C10—C9—C14—C13	−0.7 (4)
C3—C4—C5—C6	−1.9 (4)	N2—C9—C14—C13	179.2 (2)
C4—C5—C6—C7	0.7 (4)	C8—C7—N1—N2	−175.7 (2)
C5—C6—C7—C8	1.5 (4)	C6—C7—N1—N2	3.0 (3)
C5—C6—C7—N1	−177.1 (2)	C7—N1—N2—C9	179.22 (18)
C6—C7—C8—C3	−2.7 (3)	C10—C9—N2—N1	176.0 (2)
N1—C7—C8—C3	176.1 (2)	C14—C9—N2—N1	−3.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.83	2.550 (3)	146