Crystal structure of 4-amino-2,6-di-chloro-phenol.

The title compound, C6H5Cl2NO, has a single planar mol-ecule in the asymmetric unit with the non-H atoms possessing a mean deviation from planarity of 0.020 Å. In the crystal, O-H⋯N hydrogen bonds lead to the formation of infinite chains along [101] which are further linked by N-H⋯O hydrogen bonds, forming (010) sheets.

Related literature

For the crystal structure of the parent p-amino­phenol, see: Brown (1951 ▸). For other related structures, see: Ermer & Eling (1994 ▸); Dey et al. (2005 ▸); Bacchi et al. (2009 ▸).

Experimental

Crystal data

C6H5Cl2NO

M = 178.02

Monoclinic,

a = 4.6064 (5) Å

b = 11.7569 (12) Å

c = 13.2291 (13) Å

β = 96.760 (5)°

V = 711.47 (13) Å3

Z = 4

Cu Kα radiation

μ = 7.59 mm−1

T = 120 K

0.4 × 0.2 × 0.1 mm

Data collection

Bruker D8 Venture CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.425, T max = 0.754

7481 measured reflections

1402 independent reflections

1273 reflections with I ≥ 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.05

1402 reflections

99 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸) and OLEX2.refine (Bourhis et al., 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015009172/ff2137sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009172/ff2137Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009172/ff2137Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009172/ff2137fig1.tif

Mol­ecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S2056989015009172/ff2137fig2.tif

Mol­ecular packing of the title compound with hydrogen bonding shown as dashed lines.

CCDC reference: 1400729

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H5Cl2NO	F(000) = 363.7579
Mr = 178.02	Dx = 1.662 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 5198 reflections
a = 4.6064 (5) Å	θ = 5.1–72.2°
b = 11.7569 (12) Å	µ = 7.59 mm−1
c = 13.2291 (13) Å	T = 120 K
β = 96.760 (5)°	Plate, colourless
V = 711.47 (13) Å3	0.4 × 0.2 × 0.1 mm
Z = 4

Bruker D8 Venture CMOS diffractometer	1402 independent reflections
Radiation source: microfocus Cu	1273 reflections with I≥ 2σ(I)
HELIOS MX monochromator	Rint = 0.043
Detector resolution: 102.4 pixels mm-1	θmax = 72.2°, θmin = 5.1°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −14→14
Tmin = 0.425, Tmax = 0.754	l = −12→16
7481 measured reflections

Refinement on F2	2 restraints
Least-squares matrix: full	7 constraints
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.1912P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1402 reflections	Δρmax = 0.33 e Å−3
99 parameters	Δρmin = −0.35 e Å−3

Experimental. Absorption correction: SADABS-2014/4 (Bruker, 2014) was used for absorption correction. wR2(int) was 0.1370 before and 0.0641 after correction. The Ratio of minimum to maximum transmission is 0.5642. The λ/2 correction factor is 0.00150.

	x	y	z	Uiso*/Ueq
Cl1	0.10618 (10)	0.09750 (4)	0.70434 (3)	0.02213 (17)
Cl2	0.79187 (11)	0.44532 (4)	0.61176 (4)	0.02666 (18)
O1	0.4519 (3)	0.30303 (12)	0.74687 (10)	0.0214 (3)
N1	0.4522 (4)	0.13356 (14)	0.35171 (12)	0.0199 (4)
C1	0.4563 (4)	0.26523 (16)	0.65055 (14)	0.0176 (4)
C4	0.4607 (4)	0.17796 (16)	0.45234 (13)	0.0176 (4)
C5	0.6112 (4)	0.27756 (16)	0.48060 (14)	0.0196 (4)
H5	0.7170 (4)	0.31620 (16)	0.43359 (14)	0.0235 (5)*
C2	0.3011 (4)	0.16753 (16)	0.61822 (14)	0.0171 (4)
C3	0.3014 (4)	0.12337 (16)	0.52110 (14)	0.0182 (4)
H3	0.1938 (4)	0.05638 (16)	0.50165 (14)	0.0219 (5)*
C6	0.6052 (4)	0.31990 (16)	0.57788 (14)	0.0179 (4)
H1	0.615 (5)	0.329 (2)	0.7732 (18)	0.0215 (5)*
H1a	0.601 (3)	0.1551 (19)	0.3217 (15)	0.0215 (5)*
H1b	0.451 (5)	0.0598 (4)	0.3523 (17)	0.0215 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0232 (3)	0.0246 (3)	0.0204 (3)	−0.00409 (16)	0.00988 (19)	0.00083 (17)
Cl2	0.0334 (3)	0.0245 (3)	0.0225 (3)	−0.01014 (19)	0.0052 (2)	−0.00026 (18)
O1	0.0193 (6)	0.0298 (7)	0.0156 (7)	−0.0039 (6)	0.0046 (5)	−0.0042 (6)
N1	0.0206 (8)	0.0247 (9)	0.0151 (8)	0.0013 (6)	0.0057 (6)	−0.0009 (6)
C1	0.0146 (8)	0.0225 (9)	0.0159 (9)	0.0027 (7)	0.0023 (7)	0.0008 (7)
C4	0.0138 (8)	0.0248 (9)	0.0142 (9)	0.0050 (7)	0.0009 (7)	0.0005 (7)
C5	0.0177 (9)	0.0244 (10)	0.0173 (9)	0.0005 (7)	0.0048 (7)	0.0054 (7)
C2	0.0144 (8)	0.0215 (9)	0.0163 (9)	0.0011 (7)	0.0051 (7)	0.0035 (7)
C3	0.0148 (8)	0.0217 (9)	0.0185 (10)	0.0005 (7)	0.0029 (7)	−0.0007 (7)
C6	0.0158 (8)	0.0188 (9)	0.0194 (9)	−0.0007 (7)	0.0026 (7)	0.0016 (7)

Cl1—C2	1.7387 (18)	C1—C6	1.401 (3)
Cl2—C6	1.7389 (19)	C4—C5	1.389 (3)
O1—C1	1.352 (2)	C4—C3	1.391 (3)
O1—H1	0.85 (2)	C5—H5	0.9500
N1—C4	1.426 (2)	C5—C6	1.383 (3)
N1—H1a	0.870 (5)	C2—C3	1.386 (3)
N1—H1b	0.867 (5)	C3—H3	0.9500
C1—C2	1.393 (3)
H1—O1—C1	113.3 (16)	C6—C5—C4	119.33 (17)
H1a—N1—C4	112.6 (15)	C6—C5—H5	120.34 (11)
H1b—N1—C4	110.9 (15)	C1—C2—Cl1	118.37 (14)
H1b—N1—H1a	108 (2)	C3—C2—Cl1	119.15 (14)
C2—C1—O1	119.75 (16)	C3—C2—C1	122.47 (16)
C6—C1—O1	123.97 (17)	C2—C3—C4	119.44 (18)
C6—C1—C2	116.26 (17)	H3—C3—C4	120.28 (11)
C5—C4—N1	121.18 (17)	H3—C3—C2	120.28 (11)
C3—C4—N1	118.87 (18)	C1—C6—Cl2	118.64 (14)
C3—C4—C5	119.85 (17)	C5—C6—Cl2	118.79 (14)
H5—C5—C4	120.34 (10)	C5—C6—C1	122.57 (17)
Cl1—C2—C3—C4	−178.98 (14)	C4—C5—C6—Cl2	−179.43 (14)
O1—C1—C2—Cl1	−0.1 (2)	C4—C5—C6—C1	1.0 (3)
O1—C1—C2—C3	−178.74 (17)	C5—C4—C3—C2	−1.7 (3)
O1—C1—C6—Cl2	−1.1 (3)	C2—C1—C6—Cl2	177.57 (13)
O1—C1—C6—C5	178.43 (17)	C2—C1—C6—C5	−2.9 (3)
N1—C4—C5—C6	177.70 (17)	C3—C4—C5—C6	1.3 (3)
N1—C4—C3—C2	−178.14 (17)	C6—C1—C2—Cl1	−178.80 (13)
C1—C2—C3—C4	−0.3 (3)	C6—C1—C2—C3	2.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.85 (2)	1.82 (2)	2.653 (2)	168 (2)
N1—H1a···O1ii	0.87 (1)	2.05 (1)	2.921 (2)	177 (2)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1N1i	0.85(2)	1.82(2)	2.653(2)	168(2)
N1H1aO1ii	0.87(1)	2.05(1)	2.921(2)	177(2)

Symmetry codes: (i) ; (ii) .