Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617001031/sj4082sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2414314617001031/sj4082Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617001031/sj4082Isup3.cml |
CCDC reference: 1528716
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.158
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5855 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low . 0.976 Note PLAT397_ALERT_2_C Deviating C-O-C Angle from 120 Deg for O1 106.4 Degree PLAT397_ALERT_2_C Deviating C-O-C Angle from 120 Deg for O2 105.6 Degree PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.586 56 Report
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do ! PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.12 Report PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT431_ALERT_2_G Short Inter HL..A Contact Cl1 .. O2 .. 3.02 Ang. PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still 78 % Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 2 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 3 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).
C16H10Cl2O3 | F(000) = 656 |
Mr = 321.14 | Dx = 1.568 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 2086 reflections |
a = 10.1854 (7) Å | θ = 4.4–64.5° |
b = 11.0820 (8) Å | µ = 4.36 mm−1 |
c = 12.2077 (9) Å | T = 296 K |
β = 99.068 (3)° | Rectangle, white |
V = 1360.72 (17) Å3 | 0.28 × 0.26 × 0.24 mm |
Z = 4 |
Bruker X8 Proteum diffractometer | 2232 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 2086 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.048 |
Detector resolution: 18.4 pixels mm-1 | θmax = 64.5°, θmin = 4.4° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −10→12 |
Tmin = 0.375, Tmax = 0.421 | l = −14→13 |
8712 measured reflections |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1218P)2 + 0.554P] where P = (Fo2 + 2Fc2)/3 |
2232 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.13750 (6) | 0.03536 (6) | 0.24874 (5) | 0.0316 (3) | |
Cl2 | −0.37087 (6) | −0.00563 (6) | 0.38206 (6) | 0.0377 (3) | |
O1 | 0.76711 (18) | 0.39765 (18) | 0.31535 (15) | 0.0353 (6) | |
O2 | 0.80348 (18) | 0.45912 (17) | 0.49834 (15) | 0.0322 (6) | |
O3 | 0.3035 (2) | 0.20086 (19) | 0.24062 (16) | 0.0393 (7) | |
C1 | 0.8544 (3) | 0.4624 (2) | 0.3945 (2) | 0.0304 (8) | |
C2 | 0.6590 (2) | 0.3683 (2) | 0.3649 (2) | 0.0260 (7) | |
C3 | 0.5445 (2) | 0.3131 (2) | 0.3184 (2) | 0.0272 (8) | |
C4 | 0.4480 (2) | 0.2919 (2) | 0.3881 (2) | 0.0261 (7) | |
C5 | 0.4743 (3) | 0.3250 (2) | 0.4999 (2) | 0.0273 (7) | |
C6 | 0.5927 (2) | 0.3814 (2) | 0.5459 (2) | 0.0282 (7) | |
C7 | 0.3208 (3) | 0.2367 (2) | 0.3373 (2) | 0.0292 (8) | |
C8 | 0.2132 (3) | 0.2262 (3) | 0.4053 (2) | 0.0353 (8) | |
C9 | 0.1024 (3) | 0.1677 (2) | 0.3710 (2) | 0.0287 (8) | |
C10 | −0.0084 (2) | 0.1487 (2) | 0.4320 (2) | 0.0252 (7) | |
C11 | −0.1248 (2) | 0.0878 (2) | 0.3834 (2) | 0.0255 (7) | |
C12 | −0.2286 (2) | 0.0698 (2) | 0.4426 (2) | 0.0273 (8) | |
C13 | −0.2211 (3) | 0.1102 (2) | 0.5504 (2) | 0.0311 (8) | |
C14 | −0.1074 (3) | 0.1695 (2) | 0.5994 (2) | 0.0311 (8) | |
C15 | −0.0023 (3) | 0.1880 (2) | 0.5422 (2) | 0.0284 (8) | |
C16 | 0.6823 (2) | 0.4034 (2) | 0.4754 (2) | 0.0256 (7) | |
H1 | 0.86110 | 0.54520 | 0.37040 | 0.0360* | |
H3 | 0.94230 | 0.42640 | 0.40360 | 0.0360* | |
H5 | 0.41090 | 0.30880 | 0.54500 | 0.0330* | |
H6 | 0.61000 | 0.40300 | 0.62040 | 0.0340* | |
H8 | 0.22450 | 0.26250 | 0.47490 | 0.0420* | |
H9 | 0.09340 | 0.13470 | 0.30020 | 0.0340* | |
H10 | 0.53010 | 0.29020 | 0.24420 | 0.0330* | |
H13 | −0.29130 | 0.09770 | 0.58940 | 0.0370* | |
H14 | −0.10160 | 0.19730 | 0.67180 | 0.0370* | |
H15 | 0.07360 | 0.22720 | 0.57720 | 0.0340* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0261 (4) | 0.0429 (5) | 0.0243 (4) | −0.0032 (2) | −0.0007 (3) | −0.0032 (2) |
Cl2 | 0.0241 (4) | 0.0427 (5) | 0.0458 (5) | −0.0060 (3) | 0.0038 (3) | −0.0033 (3) |
O1 | 0.0295 (10) | 0.0491 (11) | 0.0295 (10) | −0.0069 (8) | 0.0113 (8) | −0.0014 (8) |
O2 | 0.0233 (10) | 0.0450 (11) | 0.0277 (10) | −0.0076 (8) | 0.0026 (8) | 0.0003 (8) |
O3 | 0.0365 (11) | 0.0494 (12) | 0.0314 (11) | −0.0144 (9) | 0.0039 (8) | −0.0068 (9) |
C1 | 0.0240 (13) | 0.0345 (14) | 0.0344 (15) | −0.0024 (11) | 0.0103 (11) | 0.0075 (11) |
C2 | 0.0224 (12) | 0.0284 (13) | 0.0274 (12) | 0.0036 (10) | 0.0045 (10) | 0.0040 (10) |
C3 | 0.0279 (13) | 0.0290 (13) | 0.0246 (13) | 0.0002 (10) | 0.0042 (10) | −0.0016 (10) |
C4 | 0.0240 (13) | 0.0234 (12) | 0.0303 (13) | 0.0023 (10) | 0.0027 (10) | 0.0005 (10) |
C5 | 0.0231 (12) | 0.0290 (13) | 0.0307 (13) | 0.0012 (10) | 0.0069 (10) | 0.0051 (10) |
C6 | 0.0273 (13) | 0.0342 (13) | 0.0229 (12) | 0.0005 (11) | 0.0037 (10) | 0.0023 (10) |
C7 | 0.0282 (14) | 0.0260 (12) | 0.0334 (14) | −0.0007 (10) | 0.0048 (11) | 0.0015 (10) |
C8 | 0.0293 (14) | 0.0390 (15) | 0.0387 (15) | −0.0037 (12) | 0.0092 (12) | −0.0097 (12) |
C9 | 0.0308 (14) | 0.0293 (13) | 0.0245 (12) | −0.0035 (11) | −0.0004 (11) | 0.0002 (10) |
C10 | 0.0258 (13) | 0.0201 (12) | 0.0286 (13) | 0.0010 (10) | 0.0013 (10) | 0.0026 (10) |
C11 | 0.0268 (13) | 0.0233 (12) | 0.0245 (12) | 0.0034 (10) | −0.0015 (10) | 0.0008 (10) |
C12 | 0.0218 (13) | 0.0216 (12) | 0.0369 (14) | 0.0021 (10) | −0.0005 (11) | 0.0008 (10) |
C13 | 0.0310 (14) | 0.0275 (13) | 0.0365 (14) | 0.0056 (11) | 0.0103 (11) | 0.0025 (11) |
C14 | 0.0392 (15) | 0.0249 (13) | 0.0302 (13) | −0.0001 (11) | 0.0086 (11) | −0.0031 (10) |
C15 | 0.0320 (14) | 0.0237 (13) | 0.0280 (13) | −0.0030 (10) | −0.0001 (10) | −0.0003 (10) |
C16 | 0.0217 (12) | 0.0251 (12) | 0.0286 (13) | 0.0015 (10) | −0.0002 (10) | 0.0043 (10) |
Cl1—C11 | 1.729 (2) | C10—C11 | 1.411 (3) |
Cl2—C12 | 1.734 (2) | C10—C15 | 1.406 (3) |
O1—C1 | 1.403 (3) | C11—C12 | 1.386 (3) |
O1—C2 | 1.376 (3) | C12—C13 | 1.381 (3) |
O2—C1 | 1.444 (3) | C13—C14 | 1.383 (4) |
O2—C16 | 1.369 (3) | C14—C15 | 1.383 (4) |
O3—C7 | 1.231 (3) | C1—H1 | 0.9700 |
C2—C3 | 1.359 (3) | C1—H3 | 0.9700 |
C2—C16 | 1.388 (3) | C3—H10 | 0.9300 |
C3—C4 | 1.417 (3) | C5—H5 | 0.9300 |
C4—C5 | 1.398 (3) | C6—H6 | 0.9300 |
C4—C7 | 1.478 (4) | C8—H8 | 0.9300 |
C5—C6 | 1.395 (4) | C9—H9 | 0.9300 |
C6—C16 | 1.371 (3) | C13—H13 | 0.9300 |
C7—C8 | 1.480 (4) | C14—H14 | 0.9300 |
C8—C9 | 1.312 (4) | C15—H15 | 0.9300 |
C9—C10 | 1.462 (4) | ||
C1—O1—C2 | 106.40 (19) | C13—C14—C15 | 121.0 (2) |
C1—O2—C16 | 105.59 (19) | C10—C15—C14 | 121.1 (2) |
O1—C1—O2 | 108.4 (2) | O2—C16—C2 | 109.62 (19) |
O1—C2—C3 | 128.0 (2) | O2—C16—C6 | 128.3 (2) |
O1—C2—C16 | 109.56 (19) | C2—C16—C6 | 122.1 (2) |
C3—C2—C16 | 122.4 (2) | O1—C1—H1 | 110.00 |
C2—C3—C4 | 117.0 (2) | O1—C1—H3 | 110.00 |
C3—C4—C5 | 119.9 (2) | O2—C1—H1 | 110.00 |
C3—C4—C7 | 117.5 (2) | O2—C1—H3 | 110.00 |
C5—C4—C7 | 122.6 (2) | H1—C1—H3 | 108.00 |
C4—C5—C6 | 122.1 (2) | C2—C3—H10 | 122.00 |
C5—C6—C16 | 116.5 (2) | C4—C3—H10 | 121.00 |
O3—C7—C4 | 121.3 (3) | C4—C5—H5 | 119.00 |
O3—C7—C8 | 120.4 (3) | C6—C5—H5 | 119.00 |
C4—C7—C8 | 118.4 (2) | C5—C6—H6 | 122.00 |
C7—C8—C9 | 122.4 (2) | C16—C6—H6 | 122.00 |
C8—C9—C10 | 127.1 (2) | C7—C8—H8 | 119.00 |
C9—C10—C11 | 121.3 (2) | C9—C8—H8 | 119.00 |
C9—C10—C15 | 121.4 (2) | C8—C9—H9 | 116.00 |
C11—C10—C15 | 117.3 (2) | C10—C9—H9 | 116.00 |
Cl1—C11—C10 | 119.50 (17) | C12—C13—H13 | 121.00 |
Cl1—C11—C12 | 119.90 (17) | C14—C13—H13 | 121.00 |
C10—C11—C12 | 120.6 (2) | C13—C14—H14 | 120.00 |
Cl2—C12—C11 | 120.14 (18) | C15—C14—H14 | 120.00 |
Cl2—C12—C13 | 118.65 (19) | C10—C15—H15 | 120.00 |
C11—C12—C13 | 121.2 (2) | C14—C15—H15 | 119.00 |
C12—C13—C14 | 118.9 (2) | ||
C2—O1—C1—O2 | 6.8 (2) | C5—C6—C16—O2 | 178.6 (2) |
C1—O1—C2—C3 | 174.9 (2) | C5—C6—C16—C2 | −2.0 (3) |
C1—O1—C2—C16 | −5.4 (3) | O3—C7—C8—C9 | 7.6 (4) |
C16—O2—C1—O1 | −5.7 (2) | C4—C7—C8—C9 | −172.9 (3) |
C1—O2—C16—C2 | 2.4 (2) | C7—C8—C9—C10 | 178.1 (2) |
C1—O2—C16—C6 | −178.1 (2) | C8—C9—C10—C11 | 177.4 (3) |
O1—C2—C3—C4 | 179.5 (2) | C8—C9—C10—C15 | −4.0 (4) |
C16—C2—C3—C4 | −0.2 (3) | C9—C10—C11—Cl1 | −0.4 (3) |
O1—C2—C16—O2 | 1.8 (3) | C9—C10—C11—C12 | 179.6 (2) |
O1—C2—C16—C6 | −177.7 (2) | C15—C10—C11—Cl1 | −179.11 (17) |
C3—C2—C16—O2 | −178.5 (2) | C15—C10—C11—C12 | 0.9 (3) |
C3—C2—C16—C6 | 2.0 (4) | C9—C10—C15—C14 | −179.9 (2) |
C2—C3—C4—C5 | −1.5 (3) | C11—C10—C15—C14 | −1.2 (3) |
C2—C3—C4—C7 | 177.4 (2) | Cl1—C11—C12—Cl2 | 0.2 (3) |
C3—C4—C5—C6 | 1.4 (3) | Cl1—C11—C12—C13 | 179.73 (18) |
C7—C4—C5—C6 | −177.4 (2) | C10—C11—C12—Cl2 | −179.78 (17) |
C3—C4—C7—O3 | 6.2 (3) | C10—C11—C12—C13 | −0.3 (3) |
C3—C4—C7—C8 | −173.3 (2) | Cl2—C12—C13—C14 | 179.45 (18) |
C5—C4—C7—O3 | −175.0 (2) | C11—C12—C13—C14 | −0.1 (3) |
C5—C4—C7—C8 | 5.5 (3) | C12—C13—C14—C15 | −0.3 (4) |
C4—C5—C6—C16 | 0.3 (3) | C13—C14—C15—C10 | 0.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Cl1 | 0.93 | 2.58 | 3.033 (3) | 110 |
C9—H9···O3 | 0.93 | 2.48 | 2.809 (4) | 101 |
C14—H14···O1i | 0.93 | 2.59 | 3.194 (3) | 123 |
Symmetry code: (i) x−1, −y+1/2, z+1/2. |