(E)-4-[(4-Chloro­phen­yl)diazen­yl]-2-isopropyl­phenol

In the title compound, C₁₅H₁₅ClN₂O, the aromatic rings adopt a trans configuration with respect to the N=N bond, as found for other diazene derivatives. The crystal structure is stabilized by inter­molecular O—H...N hydrogen bonds, forming a polymeric chain along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm

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

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-4-[(4-Chlorophenyl)diazenyl]-2-isopropylphenol

Crystal data

C15H15ClN2O	F(000) = 576
Mr = 274.74	Dx = 1.296 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 28365 reflections
a = 10.4856 (5) Å	θ = 1.9–28.0°
b = 11.1262 (6) Å	µ = 0.27 mm^−1
c = 12.0768 (5) Å	T = 296 K
β = 91.585 (4)°	Prism, brown
V = 1408.40 (12) Å^3	0.70 × 0.64 × 0.51 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	2762 independent reflections
Radiation source: fine-focus sealed tube	2455 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.9°
ω scans	h = −12→12
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −13→13
Tmin = 0.842, Tmax = 0.906	l = −14→14
19848 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)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 0.176P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
2762 reflections	Δρmax = 0.45 e Å^−3
233 parameters	Δρmin = −0.33 e Å^−3
0 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: 0.071 (6)

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
H6	0.2347 (17)	0.7464 (16)	0.4732 (15)	0.064 (5)*
H3	0.5500 (16)	0.9049 (15)	0.2665 (15)	0.057 (4)*
H14	0.0271 (18)	0.3487 (18)	−0.2116 (17)	0.078 (6)*
H2B	0.484 (2)	1.044 (2)	0.1238 (17)	0.084 (6)*
H9	0.3965 (15)	0.6726 (15)	0.1237 (14)	0.058 (4)*
H1C	0.655 (2)	0.879 (2)	0.1013 (19)	0.096 (7)*
H7	0.1672 (17)	0.5767 (15)	0.3727 (14)	0.060 (4)*
H2A	0.371 (2)	0.952 (2)	0.087 (2)	0.097 (7)*
H15	0.140 (2)	0.5010 (19)	−0.1176 (16)	0.079 (6)*
H12	0.0688 (19)	0.1344 (19)	0.0604 (17)	0.078 (6)*
H1B	0.544 (2)	0.795 (2)	0.053 (2)	0.098 (7)*
H11	0.1818 (18)	0.2879 (17)	0.1495 (17)	0.072 (5)*
H1A	0.635 (2)	0.746 (3)	0.157 (2)	0.100 (8)*
H2C	0.375 (2)	1.018 (2)	0.207 (2)	0.097 (7)*
H1	0.352 (2)	0.922 (2)	0.4640 (19)	0.085 (6)*
Cl1	−0.05269 (5)	0.11757 (4)	−0.14832 (4)	0.0815 (2)
O1	0.39874 (12)	0.90860 (10)	0.41089 (9)	0.0614 (3)
N2	0.23314 (11)	0.50803 (10)	0.07837 (9)	0.0495 (3)
N1	0.21547 (11)	0.51304 (11)	0.18066 (9)	0.0504 (3)
C9	0.36370 (13)	0.68802 (13)	0.19424 (11)	0.0476 (3)
C7	0.22621 (15)	0.63320 (14)	0.34187 (12)	0.0526 (3)
C8	0.27153 (13)	0.61174 (12)	0.23668 (11)	0.0466 (3)
C5	0.35605 (13)	0.80956 (13)	0.35630 (11)	0.0484 (3)
C6	0.26741 (15)	0.73222 (14)	0.40071 (11)	0.0540 (4)
C4	0.40717 (12)	0.78721 (12)	0.25185 (10)	0.0466 (3)
C10	0.16971 (13)	0.40833 (12)	0.02605 (11)	0.0493 (3)
C14	0.05854 (16)	0.33525 (15)	−0.13611 (14)	0.0602 (4)
C13	0.03752 (14)	0.22888 (14)	−0.08216 (13)	0.0575 (4)
C15	0.12646 (16)	0.42496 (15)	−0.08207 (12)	0.0574 (4)
C12	0.08494 (18)	0.20888 (16)	0.02394 (15)	0.0668 (4)
C11	0.15018 (17)	0.29976 (15)	0.07856 (13)	0.0617 (4)
C3	0.50135 (15)	0.87509 (15)	0.20465 (13)	0.0571 (4)
C2	0.4300 (2)	0.98012 (18)	0.15176 (18)	0.0759 (5)
C1	0.5913 (2)	0.8181 (2)	0.1231 (2)	0.0843 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0778 (3)	0.0715 (3)	0.0947 (4)	−0.0107 (2)	−0.0057 (2)	−0.0264 (2)
O1	0.0744 (7)	0.0610 (6)	0.0494 (6)	−0.0070 (5)	0.0108 (5)	−0.0125 (5)
N2	0.0543 (6)	0.0499 (6)	0.0442 (6)	−0.0009 (5)	0.0015 (5)	0.0015 (5)
N1	0.0515 (6)	0.0547 (7)	0.0452 (6)	−0.0021 (5)	0.0042 (5)	0.0006 (5)
C9	0.0486 (7)	0.0553 (7)	0.0392 (6)	0.0003 (6)	0.0052 (5)	−0.0008 (5)
C7	0.0536 (8)	0.0592 (8)	0.0453 (7)	−0.0036 (6)	0.0080 (6)	0.0036 (6)
C8	0.0487 (7)	0.0491 (7)	0.0421 (6)	0.0005 (5)	0.0014 (5)	0.0011 (5)
C5	0.0520 (7)	0.0517 (7)	0.0415 (6)	0.0034 (6)	0.0018 (5)	−0.0019 (5)
C6	0.0593 (8)	0.0631 (8)	0.0400 (7)	−0.0005 (6)	0.0099 (6)	−0.0018 (6)
C4	0.0463 (7)	0.0531 (7)	0.0405 (6)	0.0012 (5)	0.0024 (5)	0.0011 (5)
C10	0.0494 (7)	0.0510 (7)	0.0476 (7)	−0.0012 (6)	0.0043 (6)	−0.0010 (6)
C14	0.0619 (9)	0.0647 (9)	0.0534 (8)	0.0061 (7)	−0.0052 (7)	−0.0068 (7)
C13	0.0501 (8)	0.0583 (8)	0.0642 (9)	0.0003 (6)	0.0053 (6)	−0.0137 (7)
C15	0.0667 (9)	0.0543 (8)	0.0510 (8)	0.0012 (7)	−0.0014 (7)	0.0017 (6)
C12	0.0782 (11)	0.0568 (9)	0.0658 (10)	−0.0124 (8)	0.0066 (8)	0.0027 (7)
C11	0.0756 (10)	0.0599 (9)	0.0493 (8)	−0.0099 (7)	−0.0007 (7)	0.0049 (6)
C3	0.0570 (8)	0.0668 (9)	0.0478 (7)	−0.0146 (7)	0.0064 (6)	−0.0046 (6)
C2	0.0916 (13)	0.0662 (11)	0.0701 (11)	−0.0172 (10)	0.0035 (10)	0.0119 (9)
C1	0.0739 (12)	0.0951 (15)	0.0857 (14)	−0.0217 (12)	0.0334 (11)	−0.0118 (12)

Geometric parameters (Å, º)

Cl1—C13	1.7392 (15)	C14—C13	1.372 (2)
O1—C5	1.3539 (17)	C14—C15	1.380 (2)
O1—H1	0.84 (2)	C14—H14	0.97 (2)
N2—N1	1.2554 (16)	C13—C12	1.380 (2)
N2—C10	1.4314 (18)	C15—H15	0.96 (2)
N1—C8	1.4096 (17)	C12—C11	1.379 (2)
C9—C4	1.3756 (19)	C12—H12	0.96 (2)
C9—C8	1.3944 (19)	C11—H11	0.92 (2)
C9—H9	0.944 (17)	C3—C2	1.519 (3)
C7—C6	1.374 (2)	C3—C1	1.521 (3)
C7—C8	1.3893 (19)	C3—H3	0.952 (18)
C7—H7	0.965 (18)	C2—H2B	0.98 (2)
C5—C6	1.385 (2)	C2—H2A	1.03 (3)
C5—C4	1.4063 (18)	C2—H2C	0.99 (2)
C6—H6	0.962 (18)	C1—H1C	0.99 (3)
C4—C3	1.5124 (19)	C1—H1B	1.00 (2)
C10—C11	1.382 (2)	C1—H1A	1.00 (3)
C10—C15	1.383 (2)
C5—O1—H1	109.2 (16)	C12—C13—Cl1	119.30 (13)
N1—N2—C10	112.91 (11)	C14—C15—C10	120.09 (15)
N2—N1—C8	115.84 (11)	C14—C15—H15	120.5 (12)
C4—C9—C8	121.72 (12)	C10—C15—H15	119.4 (12)
C4—C9—H9	118.6 (10)	C11—C12—C13	119.17 (16)
C8—C9—H9	119.7 (10)	C11—C12—H12	120.5 (12)
C6—C7—C8	120.00 (13)	C13—C12—H12	120.3 (12)
C6—C7—H7	121.3 (10)	C12—C11—C10	119.96 (15)
C8—C7—H7	118.7 (10)	C12—C11—H11	120.1 (12)
C7—C8—C9	119.32 (13)	C10—C11—H11	119.9 (12)
C7—C8—N1	115.09 (12)	C4—C3—C2	109.66 (14)
C9—C8—N1	125.58 (12)	C4—C3—C1	113.45 (15)
O1—C5—C6	122.23 (12)	C2—C3—C1	110.83 (17)
O1—C5—C4	116.85 (12)	C4—C3—H3	105.7 (10)
C6—C5—C4	120.92 (13)	C2—C3—H3	108.0 (10)
C7—C6—C5	120.16 (12)	C1—C3—H3	109.0 (10)
C7—C6—H6	119.2 (11)	C3—C2—H2B	114.6 (13)
C5—C6—H6	120.7 (11)	C3—C2—H2A	111.1 (13)
C9—C4—C5	117.80 (12)	H2B—C2—H2A	107.7 (18)
C9—C4—C3	122.60 (12)	C3—C2—H2C	109.5 (14)
C5—C4—C3	119.52 (12)	H2B—C2—H2C	106.1 (18)
C11—C10—C15	120.08 (14)	H2A—C2—H2C	107 (2)
C11—C10—N2	123.21 (13)	C3—C1—H1C	108.9 (13)
C15—C10—N2	116.71 (12)	C3—C1—H1B	110.6 (14)
C13—C14—C15	119.15 (15)	H1C—C1—H1B	105.7 (19)
C13—C14—H14	121.5 (12)	C3—C1—H1A	110.4 (14)
C15—C14—H14	119.3 (12)	H1C—C1—H1A	110.5 (19)
C14—C13—C12	121.45 (15)	H1B—C1—H1A	111 (2)
C14—C13—Cl1	119.25 (12)
C10—N2—N1—C8	−177.76 (11)	N1—N2—C10—C11	−31.99 (19)
C6—C7—C8—C9	3.3 (2)	N1—N2—C10—C15	147.60 (13)
C6—C7—C8—N1	−175.29 (13)	C15—C14—C13—C12	−1.3 (2)
C4—C9—C8—C7	−2.8 (2)	C15—C14—C13—Cl1	177.82 (12)
C4—C9—C8—N1	175.57 (13)	C13—C14—C15—C10	−1.6 (2)
N2—N1—C8—C7	164.67 (13)	C11—C10—C15—C14	3.0 (2)
N2—N1—C8—C9	−13.8 (2)	N2—C10—C15—C14	−176.60 (14)
C8—C7—C6—C5	−1.3 (2)	C14—C13—C12—C11	2.8 (3)
O1—C5—C6—C7	179.54 (14)	Cl1—C13—C12—C11	−176.32 (13)
C4—C5—C6—C7	−1.3 (2)	C13—C12—C11—C10	−1.4 (3)
C8—C9—C4—C5	0.4 (2)	C15—C10—C11—C12	−1.5 (2)
C8—C9—C4—C3	−176.37 (13)	N2—C10—C11—C12	178.09 (15)
O1—C5—C4—C9	−179.05 (12)	C9—C4—C3—C2	95.11 (18)
C6—C5—C4—C9	1.7 (2)	C5—C4—C3—C2	−81.56 (17)
O1—C5—C4—C3	−2.2 (2)	C9—C4—C3—C1	−29.4 (2)
C6—C5—C4—C3	178.53 (14)	C5—C4—C3—C1	153.93 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2^i	0.84 (2)	2.04 (2)	2.8566 (16)	168 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.