Download citation
Download citation
link to html
The title structure, C12H8Cl2O2, is a putative metabolite of 3,5-di­chloro­biphenyl (PCB 14). The dihedral angle between the two benzene rings of the title compounds is 58.86 (4)°. In the crystal, it displays intra- and inter­molecular O—H...O hydrogen bonding and inter­molecular O—H...Cl hydrogen...chlorine inter­actions. The inter­molecular inter­actions form a two-dimensional network parallel to (010).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619012021/lh4050sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314619012021/lh4050Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619012021/lh4050Isup3.cml
Supplementary material

CCDC reference: 1950307

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.074
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.471 Check
Alert level G PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 3 Info PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 12 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 2006); data reduction: DENZO-SMN (Otwinowski & Minor, 2006); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL-2018/3 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013).

3-(3,5-Dichlorophenyl)benzene-1,2-diol top
Crystal data top
C12H8Cl2O2F(000) = 520
Mr = 255.08Dx = 1.569 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.2198 (3) ÅCell parameters from 5954 reflections
b = 16.9271 (8) Åθ = 1.0–27.5°
c = 10.4460 (5) ŵ = 0.58 mm1
β = 101.013 (3)°T = 90 K
V = 1079.53 (9) Å3Block, colourless
Z = 40.28 × 0.25 × 0.25 mm
Data collection top
Nonius KappaCCD
diffractometer
2470 independent reflections
Radiation source: fine-focus sealed-tube2029 reflections with I > 2σ(I)
Detector resolution: 9.1 pixels mm-1Rint = 0.037
φ and ω scans at fixed χ = 55°θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(Scalepack; Otwinowski & Minor, 2006)
h = 78
Tmin = 0.855, Tmax = 0.869k = 2121
6641 measured reflectionsl = 1113
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: difference Fourier map
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0259P)2 + 0.363P]
where P = (Fo2 + 2Fc2)/3
2470 reflections(Δ/σ)max = 0.001
149 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat.

Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

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

Refinement. H atoms were found in difference Fourier maps. Carbon-bound H atoms were subsequently included in the refinement using riding models, with constrained distances set to 0.95 Å (Csp2H). Hydroxyl O—H distances were refined. Uiso(H) parameters were set to values of either 1.2Ueq or 1.5Ueq (OH only) of the attached atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.06252 (7)0.51040 (2)0.70416 (4)0.02025 (12)
Cl20.30147 (7)0.35884 (3)0.52162 (4)0.02112 (13)
O10.98156 (18)0.29232 (7)1.03073 (11)0.0180 (3)
H1O1.064 (3)0.2671 (12)1.0814 (15)0.027*
O20.98599 (18)0.25308 (7)1.27641 (11)0.0189 (3)
H2O0.9675 (16)0.2391 (11)1.343 (2)0.028*
C10.6550 (3)0.38712 (9)0.88020 (16)0.0151 (4)
C20.8333 (3)0.43045 (9)0.85610 (16)0.0156 (4)
H20.9481280.4445850.9261130.019*
C30.8430 (3)0.45292 (10)0.72976 (16)0.0157 (4)
C40.6808 (3)0.43163 (9)0.62473 (16)0.0165 (4)
H40.6896660.4462180.5380810.020*
C50.5060 (3)0.38841 (10)0.65118 (16)0.0162 (4)
C60.4880 (3)0.36663 (9)0.77716 (16)0.0154 (4)
H60.3635330.3382400.7924450.018*
C1'0.6450 (3)0.36330 (9)1.01653 (16)0.0146 (3)
C2'0.8112 (3)0.31794 (9)1.08832 (16)0.0140 (3)
C3'0.8095 (3)0.29685 (9)1.21704 (16)0.0145 (4)
C4'0.6384 (3)0.32091 (10)1.27509 (16)0.0171 (4)
H4'0.6363530.3070081.3629590.020*
C5'0.4694 (3)0.36558 (10)1.20385 (17)0.0193 (4)
H5'0.3511570.3820461.2431620.023*
C6'0.4723 (3)0.38623 (10)1.07594 (17)0.0190 (4)
H6'0.3551340.4163881.0280580.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0179 (2)0.0205 (2)0.0225 (2)0.00488 (18)0.00431 (17)0.00181 (18)
Cl20.0210 (2)0.0269 (2)0.0137 (2)0.00667 (18)0.00082 (17)0.00019 (17)
O10.0150 (6)0.0252 (7)0.0139 (6)0.0082 (5)0.0030 (5)0.0026 (5)
O20.0195 (6)0.0251 (7)0.0123 (6)0.0048 (5)0.0041 (5)0.0055 (5)
C10.0169 (8)0.0130 (8)0.0150 (8)0.0045 (7)0.0022 (7)0.0008 (7)
C20.0149 (8)0.0138 (8)0.0170 (8)0.0020 (7)0.0000 (7)0.0026 (7)
C30.0151 (8)0.0113 (8)0.0211 (9)0.0004 (7)0.0045 (7)0.0002 (7)
C40.0193 (9)0.0152 (8)0.0152 (8)0.0022 (7)0.0039 (7)0.0018 (7)
C50.0145 (8)0.0158 (8)0.0164 (8)0.0014 (7)0.0018 (7)0.0021 (7)
C60.0143 (8)0.0140 (8)0.0183 (9)0.0003 (7)0.0041 (7)0.0001 (7)
C1'0.0157 (8)0.0138 (8)0.0135 (8)0.0017 (7)0.0008 (7)0.0011 (7)
C2'0.0139 (8)0.0154 (8)0.0134 (8)0.0024 (7)0.0045 (7)0.0047 (7)
C3'0.0156 (8)0.0116 (8)0.0153 (8)0.0019 (7)0.0006 (7)0.0002 (7)
C4'0.0201 (9)0.0176 (8)0.0142 (8)0.0041 (7)0.0052 (7)0.0006 (7)
C5'0.0182 (9)0.0215 (9)0.0198 (9)0.0010 (8)0.0079 (7)0.0029 (7)
C6'0.0171 (9)0.0201 (9)0.0199 (9)0.0030 (7)0.0040 (7)0.0005 (7)
Geometric parameters (Å, º) top
Cl1—C31.7386 (17)C4—H40.9500
Cl2—C51.7445 (16)C5—C61.392 (2)
O1—C2'1.3842 (18)C6—H60.9500
O1—H1O0.79 (2)C1'—C2'1.387 (2)
O2—C3'1.3704 (19)C1'—C6'1.395 (2)
O2—H2O0.77 (2)C2'—C3'1.393 (2)
C1—C61.390 (2)C3'—C4'1.383 (2)
C1—C21.392 (2)C4'—C5'1.390 (2)
C1—C1'1.493 (2)C4'—H4'0.9500
C2—C31.386 (2)C5'—C6'1.385 (2)
C2—H20.9500C5'—H5'0.9500
C3—C41.389 (2)C6'—H6'0.9500
C4—C51.381 (2)
C2'—O1—H1O109.5C5—C6—H6120.6
C3'—O2—H2O109.5C2'—C1'—C6'118.12 (15)
C6—C1—C2119.67 (15)C2'—C1'—C1120.19 (15)
C6—C1—C1'120.70 (15)C6'—C1'—C1121.69 (15)
C2—C1—C1'119.64 (15)O1—C2'—C1'119.45 (14)
C3—C2—C1119.85 (15)O1—C2'—C3'119.12 (14)
C3—C2—H2120.1C1'—C2'—C3'121.42 (15)
C1—C2—H2120.1O2—C3'—C4'125.29 (15)
C2—C3—C4121.61 (15)O2—C3'—C2'114.97 (14)
C2—C3—Cl1118.58 (13)C4'—C3'—C2'119.73 (15)
C4—C3—Cl1119.81 (13)C3'—C4'—C5'119.48 (15)
C5—C4—C3117.39 (15)C3'—C4'—H4'120.3
C5—C4—H4121.3C5'—C4'—H4'120.3
C3—C4—H4121.3C6'—C5'—C4'120.41 (16)
C4—C5—C6122.57 (15)C6'—C5'—H5'119.8
C4—C5—Cl2118.82 (13)C4'—C5'—H5'119.8
C6—C5—Cl2118.61 (13)C5'—C6'—C1'120.82 (16)
C1—C6—C5118.87 (15)C5'—C6'—H6'119.6
C1—C6—H6120.6C1'—C6'—H6'119.6
C6—C1—C2—C30.1 (2)C2—C1—C1'—C6'121.12 (18)
C1'—C1—C2—C3179.80 (15)C6'—C1'—C2'—O1178.10 (14)
C1—C2—C3—C41.6 (2)C1—C1'—C2'—O12.6 (2)
C1—C2—C3—Cl1177.41 (12)C6'—C1'—C2'—C3'1.3 (2)
C2—C3—C4—C51.3 (2)C1—C1'—C2'—C3'178.05 (15)
Cl1—C3—C4—C5177.66 (12)O1—C2'—C3'—O21.7 (2)
C3—C4—C5—C60.4 (2)C1'—C2'—C3'—O2178.96 (14)
C3—C4—C5—Cl2178.77 (12)O1—C2'—C3'—C4'178.90 (14)
C2—C1—C6—C51.6 (2)C1'—C2'—C3'—C4'0.5 (2)
C1'—C1—C6—C5178.52 (15)O2—C3'—C4'—C5'179.68 (15)
C4—C5—C6—C11.9 (2)C2'—C3'—C4'—C5'0.3 (2)
Cl2—C5—C6—C1177.29 (12)C3'—C4'—C5'—C6'0.3 (3)
C6—C1—C1'—C2'121.97 (18)C4'—C5'—C6'—C1'0.5 (3)
C2—C1—C1'—C2'58.2 (2)C2'—C1'—C6'—C5'1.3 (3)
C6—C1—C1'—C6'58.8 (2)C1—C1'—C6'—C5'178.00 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···Cl2i0.792.733.2538 (12)126
O1—H1O···O20.792.202.6459 (16)117
O2—H2O···O1ii0.772.022.7708 (16)169
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1/2, z+1/2.
 

Follow IUCrData
Sign up for e-alerts
Follow IUCrData on Twitter
Follow us on facebook
Sign up for RSS feeds