




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619012021/lh4050sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2414314619012021/lh4050Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619012021/lh4050Isup3.cml |
CCDC reference: 1950307
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean
(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
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).
C12H8Cl2O2 | F(000) = 520 |
Mr = 255.08 | Dx = 1.569 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2198 (3) Å | Cell parameters from 5954 reflections |
b = 16.9271 (8) Å | θ = 1.0–27.5° |
c = 10.4460 (5) Å | µ = 0.58 mm−1 |
β = 101.013 (3)° | T = 90 K |
V = 1079.53 (9) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.25 × 0.25 mm |
Nonius KappaCCD diffractometer | 2470 independent reflections |
Radiation source: fine-focus sealed-tube | 2029 reflections with I > 2σ(I) |
Detector resolution: 9.1 pixels mm-1 | Rint = 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 = −7→8 |
Tmin = 0.855, Tmax = 0.869 | k = −21→21 |
6641 measured reflections | l = −11→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.074 | H 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 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.06252 (7) | 0.51040 (2) | 0.70416 (4) | 0.02025 (12) | |
Cl2 | 0.30147 (7) | 0.35884 (3) | 0.52162 (4) | 0.02112 (13) | |
O1 | 0.98156 (18) | 0.29232 (7) | 1.03073 (11) | 0.0180 (3) | |
H1O | 1.064 (3) | 0.2671 (12) | 1.0814 (15) | 0.027* | |
O2 | 0.98599 (18) | 0.25308 (7) | 1.27641 (11) | 0.0189 (3) | |
H2O | 0.9675 (16) | 0.2391 (11) | 1.343 (2) | 0.028* | |
C1 | 0.6550 (3) | 0.38712 (9) | 0.88020 (16) | 0.0151 (4) | |
C2 | 0.8333 (3) | 0.43045 (9) | 0.85610 (16) | 0.0156 (4) | |
H2 | 0.948128 | 0.444585 | 0.926113 | 0.019* | |
C3 | 0.8430 (3) | 0.45292 (10) | 0.72976 (16) | 0.0157 (4) | |
C4 | 0.6808 (3) | 0.43163 (9) | 0.62473 (16) | 0.0165 (4) | |
H4 | 0.689666 | 0.446218 | 0.538081 | 0.020* | |
C5 | 0.5060 (3) | 0.38841 (10) | 0.65118 (16) | 0.0162 (4) | |
C6 | 0.4880 (3) | 0.36663 (9) | 0.77716 (16) | 0.0154 (4) | |
H6 | 0.363533 | 0.338240 | 0.792445 | 0.018* | |
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' | 0.636353 | 0.307008 | 1.362959 | 0.020* | |
C5' | 0.4694 (3) | 0.36558 (10) | 1.20385 (17) | 0.0193 (4) | |
H5' | 0.351157 | 0.382046 | 1.243162 | 0.023* | |
C6' | 0.4723 (3) | 0.38623 (10) | 1.07594 (17) | 0.0190 (4) | |
H6' | 0.355134 | 0.416388 | 1.028058 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0179 (2) | 0.0205 (2) | 0.0225 (2) | −0.00488 (18) | 0.00431 (17) | 0.00181 (18) |
Cl2 | 0.0210 (2) | 0.0269 (2) | 0.0137 (2) | −0.00667 (18) | −0.00082 (17) | −0.00019 (17) |
O1 | 0.0150 (6) | 0.0252 (7) | 0.0139 (6) | 0.0082 (5) | 0.0030 (5) | 0.0026 (5) |
O2 | 0.0195 (6) | 0.0251 (7) | 0.0123 (6) | 0.0048 (5) | 0.0041 (5) | 0.0055 (5) |
C1 | 0.0169 (8) | 0.0130 (8) | 0.0150 (8) | 0.0045 (7) | 0.0022 (7) | −0.0008 (7) |
C2 | 0.0149 (8) | 0.0138 (8) | 0.0170 (8) | 0.0020 (7) | 0.0000 (7) | −0.0026 (7) |
C3 | 0.0151 (8) | 0.0113 (8) | 0.0211 (9) | 0.0004 (7) | 0.0045 (7) | −0.0002 (7) |
C4 | 0.0193 (9) | 0.0152 (8) | 0.0152 (8) | 0.0022 (7) | 0.0039 (7) | 0.0018 (7) |
C5 | 0.0145 (8) | 0.0158 (8) | 0.0164 (8) | 0.0014 (7) | −0.0018 (7) | −0.0021 (7) |
C6 | 0.0143 (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) |
Cl1—C3 | 1.7386 (17) | C4—H4 | 0.9500 |
Cl2—C5 | 1.7445 (16) | C5—C6 | 1.392 (2) |
O1—C2' | 1.3842 (18) | C6—H6 | 0.9500 |
O1—H1O | 0.79 (2) | C1'—C2' | 1.387 (2) |
O2—C3' | 1.3704 (19) | C1'—C6' | 1.395 (2) |
O2—H2O | 0.77 (2) | C2'—C3' | 1.393 (2) |
C1—C6 | 1.390 (2) | C3'—C4' | 1.383 (2) |
C1—C2 | 1.392 (2) | C4'—C5' | 1.390 (2) |
C1—C1' | 1.493 (2) | C4'—H4' | 0.9500 |
C2—C3 | 1.386 (2) | C5'—C6' | 1.385 (2) |
C2—H2 | 0.9500 | C5'—H5' | 0.9500 |
C3—C4 | 1.389 (2) | C6'—H6' | 0.9500 |
C4—C5 | 1.381 (2) | ||
C2'—O1—H1O | 109.5 | C5—C6—H6 | 120.6 |
C3'—O2—H2O | 109.5 | C2'—C1'—C6' | 118.12 (15) |
C6—C1—C2 | 119.67 (15) | C2'—C1'—C1 | 120.19 (15) |
C6—C1—C1' | 120.70 (15) | C6'—C1'—C1 | 121.69 (15) |
C2—C1—C1' | 119.64 (15) | O1—C2'—C1' | 119.45 (14) |
C3—C2—C1 | 119.85 (15) | O1—C2'—C3' | 119.12 (14) |
C3—C2—H2 | 120.1 | C1'—C2'—C3' | 121.42 (15) |
C1—C2—H2 | 120.1 | O2—C3'—C4' | 125.29 (15) |
C2—C3—C4 | 121.61 (15) | O2—C3'—C2' | 114.97 (14) |
C2—C3—Cl1 | 118.58 (13) | C4'—C3'—C2' | 119.73 (15) |
C4—C3—Cl1 | 119.81 (13) | C3'—C4'—C5' | 119.48 (15) |
C5—C4—C3 | 117.39 (15) | C3'—C4'—H4' | 120.3 |
C5—C4—H4 | 121.3 | C5'—C4'—H4' | 120.3 |
C3—C4—H4 | 121.3 | C6'—C5'—C4' | 120.41 (16) |
C4—C5—C6 | 122.57 (15) | C6'—C5'—H5' | 119.8 |
C4—C5—Cl2 | 118.82 (13) | C4'—C5'—H5' | 119.8 |
C6—C5—Cl2 | 118.61 (13) | C5'—C6'—C1' | 120.82 (16) |
C1—C6—C5 | 118.87 (15) | C5'—C6'—H6' | 119.6 |
C1—C6—H6 | 120.6 | C1'—C6'—H6' | 119.6 |
C6—C1—C2—C3 | 0.1 (2) | C2—C1—C1'—C6' | 121.12 (18) |
C1'—C1—C2—C3 | −179.80 (15) | C6'—C1'—C2'—O1 | 178.10 (14) |
C1—C2—C3—C4 | −1.6 (2) | C1—C1'—C2'—O1 | −2.6 (2) |
C1—C2—C3—Cl1 | 177.41 (12) | C6'—C1'—C2'—C3' | −1.3 (2) |
C2—C3—C4—C5 | 1.3 (2) | C1—C1'—C2'—C3' | 178.05 (15) |
Cl1—C3—C4—C5 | −177.66 (12) | O1—C2'—C3'—O2 | 1.7 (2) |
C3—C4—C5—C6 | 0.4 (2) | C1'—C2'—C3'—O2 | −178.96 (14) |
C3—C4—C5—Cl2 | −178.77 (12) | O1—C2'—C3'—C4' | −178.90 (14) |
C2—C1—C6—C5 | 1.6 (2) | C1'—C2'—C3'—C4' | 0.5 (2) |
C1'—C1—C6—C5 | −178.52 (15) | O2—C3'—C4'—C5' | 179.68 (15) |
C4—C5—C6—C1 | −1.9 (2) | C2'—C3'—C4'—C5' | 0.3 (2) |
Cl2—C5—C6—C1 | 177.29 (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) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···Cl2i | 0.79 | 2.73 | 3.2538 (12) | 126 |
O1—H1O···O2 | 0.79 | 2.20 | 2.6459 (16) | 117 |
O2—H2O···O1ii | 0.77 | 2.02 | 2.7708 (16) | 169 |
Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) x, −y+1/2, z+1/2. |