Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039006/sj2130sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039006/sj2130Isup2.hkl |
CCDC reference: 628399
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C)= 0.002 Å
- R factor = 0.049
- wR factor = 0.116
- Data-to-parameter ratio = 34.8
checkCIF/PLATON results
No syntax errors found No errors found in this datablock 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.
Author Response: H.K. Fun and I.A. Razak are supervisors of M.M. Rosli whereas S.M. Dharmaprakash is the supervisor of P.S. Patil and Vedavati G. Puranik in this collaborative publication. Mangalore University and National Chemical Laboratory, India is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript. |
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, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C16H12Cl2O2 | F(000) = 1264 |
Mr = 307.16 | Dx = 1.475 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5935 reflections |
a = 7.1676 (1) Å | θ = 2.4–35.6° |
b = 11.1505 (2) Å | µ = 0.47 mm−1 |
c = 34.6112 (5) Å | T = 100 K |
V = 2766.21 (7) Å3 | Block, yellow |
Z = 8 | 0.49 × 0.25 × 0.23 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 6337 independent reflections |
Radiation source: fine-focus sealed tube | 4966 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 8.33 pixels mm-1 | θmax = 35.6°, θmin = 1.2° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −18→17 |
Tmin = 0.808, Tmax = 0.900 | l = −56→52 |
62000 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0435P)2 + 1.3505P] where P = (Fo2 + 2Fc2)/3 |
6337 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.44706 (6) | 0.40078 (3) | 0.063968 (9) | 0.03001 (9) | |
Cl2 | 0.47854 (6) | 0.84709 (3) | 0.007057 (10) | 0.03600 (10) | |
O1 | 0.68608 (14) | 0.33372 (8) | 0.19368 (3) | 0.02448 (19) | |
O2 | 0.61171 (15) | 0.51343 (9) | 0.36564 (3) | 0.0259 (2) | |
C1 | 0.59437 (17) | 0.57632 (10) | 0.26127 (3) | 0.0187 (2) | |
H1A | 0.5701 | 0.6387 | 0.2442 | 0.022* | |
C2 | 0.58249 (17) | 0.59731 (10) | 0.30090 (3) | 0.0195 (2) | |
H2A | 0.5507 | 0.6729 | 0.3101 | 0.023* | |
C3 | 0.61860 (17) | 0.50425 (11) | 0.32646 (3) | 0.0197 (2) | |
C4 | 0.66545 (18) | 0.39008 (11) | 0.31234 (4) | 0.0224 (2) | |
H4A | 0.6891 | 0.3276 | 0.3294 | 0.027* | |
C5 | 0.67627 (18) | 0.37105 (10) | 0.27313 (4) | 0.0205 (2) | |
H5A | 0.7070 | 0.2952 | 0.2640 | 0.025* | |
C6 | 0.64194 (16) | 0.46363 (10) | 0.24672 (3) | 0.01767 (19) | |
C7 | 0.65504 (17) | 0.43686 (10) | 0.20479 (3) | 0.0188 (2) | |
C8 | 0.62814 (18) | 0.53529 (11) | 0.17638 (3) | 0.0206 (2) | |
H8A | 0.6380 | 0.6150 | 0.1841 | 0.025* | |
C9 | 0.58965 (18) | 0.50787 (11) | 0.13961 (3) | 0.0206 (2) | |
H9A | 0.5816 | 0.4267 | 0.1336 | 0.025* | |
C10 | 0.55885 (17) | 0.59181 (11) | 0.10780 (3) | 0.0197 (2) | |
C11 | 0.49588 (19) | 0.55209 (11) | 0.07163 (4) | 0.0216 (2) | |
C12 | 0.4680 (2) | 0.62882 (12) | 0.04057 (4) | 0.0248 (2) | |
H12A | 0.4253 | 0.6000 | 0.0170 | 0.030* | |
C13 | 0.5058 (2) | 0.74996 (12) | 0.04577 (4) | 0.0251 (2) | |
C14 | 0.5654 (2) | 0.79463 (12) | 0.08119 (4) | 0.0249 (2) | |
H14A | 0.5879 | 0.8762 | 0.0844 | 0.030* | |
C15 | 0.59092 (18) | 0.71601 (11) | 0.11165 (4) | 0.0223 (2) | |
H15A | 0.6304 | 0.7459 | 0.1354 | 0.027* | |
C16 | 0.5748 (2) | 0.62859 (12) | 0.38195 (4) | 0.0261 (3) | |
H16A | 0.5674 | 0.6218 | 0.4096 | 0.039* | |
H16B | 0.4586 | 0.6586 | 0.3721 | 0.039* | |
H16C | 0.6736 | 0.6828 | 0.3752 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0471 (2) | 0.02095 (14) | 0.02200 (14) | −0.00628 (13) | −0.00572 (13) | −0.00217 (10) |
Cl2 | 0.0525 (2) | 0.02803 (17) | 0.02751 (17) | 0.00807 (15) | 0.00662 (15) | 0.00880 (12) |
O1 | 0.0299 (5) | 0.0165 (4) | 0.0270 (4) | 0.0008 (3) | 0.0007 (4) | −0.0030 (3) |
O2 | 0.0348 (5) | 0.0225 (4) | 0.0204 (4) | 0.0004 (4) | 0.0014 (4) | 0.0019 (3) |
C1 | 0.0206 (5) | 0.0146 (4) | 0.0210 (5) | −0.0004 (4) | −0.0018 (4) | 0.0013 (4) |
C2 | 0.0220 (5) | 0.0150 (5) | 0.0216 (5) | 0.0002 (4) | −0.0004 (4) | 0.0000 (4) |
C3 | 0.0202 (5) | 0.0191 (5) | 0.0197 (5) | −0.0010 (4) | 0.0001 (4) | 0.0018 (4) |
C4 | 0.0251 (6) | 0.0174 (5) | 0.0246 (5) | 0.0023 (4) | 0.0009 (4) | 0.0043 (4) |
C5 | 0.0216 (5) | 0.0142 (4) | 0.0258 (5) | 0.0011 (4) | 0.0008 (4) | 0.0017 (4) |
C6 | 0.0167 (5) | 0.0145 (4) | 0.0218 (5) | −0.0007 (4) | −0.0003 (4) | 0.0006 (4) |
C7 | 0.0175 (5) | 0.0166 (5) | 0.0223 (5) | −0.0016 (4) | −0.0004 (4) | −0.0007 (4) |
C8 | 0.0234 (5) | 0.0169 (5) | 0.0215 (5) | −0.0015 (4) | −0.0003 (4) | −0.0004 (4) |
C9 | 0.0220 (5) | 0.0182 (5) | 0.0216 (5) | −0.0006 (4) | −0.0009 (4) | −0.0014 (4) |
C10 | 0.0202 (5) | 0.0186 (5) | 0.0202 (5) | −0.0002 (4) | 0.0010 (4) | −0.0009 (4) |
C11 | 0.0257 (6) | 0.0187 (5) | 0.0203 (5) | −0.0006 (4) | 0.0011 (4) | −0.0018 (4) |
C12 | 0.0316 (7) | 0.0238 (5) | 0.0191 (5) | 0.0025 (5) | 0.0012 (5) | 0.0008 (4) |
C13 | 0.0301 (6) | 0.0225 (5) | 0.0228 (5) | 0.0048 (5) | 0.0050 (5) | 0.0038 (4) |
C14 | 0.0283 (6) | 0.0186 (5) | 0.0278 (6) | 0.0016 (5) | 0.0033 (5) | 0.0003 (4) |
C15 | 0.0232 (6) | 0.0200 (5) | 0.0239 (5) | 0.0007 (4) | 0.0008 (4) | −0.0026 (4) |
C16 | 0.0289 (7) | 0.0260 (6) | 0.0234 (6) | 0.0002 (5) | 0.0024 (5) | −0.0016 (4) |
Cl1—C11 | 1.7435 (13) | C8—C9 | 1.3373 (17) |
Cl2—C13 | 1.7340 (13) | C8—H8A | 0.9300 |
O1—C7 | 1.2329 (14) | C9—C10 | 1.4618 (17) |
O2—C3 | 1.3610 (15) | C9—H9A | 0.9300 |
O2—C16 | 1.4274 (16) | C10—C11 | 1.4026 (17) |
C1—C2 | 1.3940 (17) | C10—C15 | 1.4101 (17) |
C1—C6 | 1.3960 (16) | C11—C12 | 1.3883 (18) |
C1—H1A | 0.9300 | C12—C13 | 1.3892 (19) |
C2—C3 | 1.3880 (16) | C12—H12A | 0.9300 |
C2—H2A | 0.9300 | C13—C14 | 1.3907 (19) |
C3—C4 | 1.4042 (17) | C14—C15 | 1.3832 (18) |
C4—C5 | 1.3759 (18) | C14—H14A | 0.9300 |
C4—H4A | 0.9300 | C15—H15A | 0.9300 |
C5—C6 | 1.4006 (16) | C16—H16A | 0.9600 |
C5—H5A | 0.9300 | C16—H16B | 0.9600 |
C6—C7 | 1.4848 (17) | C16—H16C | 0.9600 |
C7—C8 | 1.4862 (17) | ||
C3—O2—C16 | 117.93 (10) | C8—C9—H9A | 116.5 |
C2—C1—C6 | 121.39 (11) | C10—C9—H9A | 116.5 |
C2—C1—H1A | 119.3 | C11—C10—C15 | 116.54 (11) |
C6—C1—H1A | 119.3 | C11—C10—C9 | 121.24 (11) |
C3—C2—C1 | 119.36 (11) | C15—C10—C9 | 122.21 (11) |
C3—C2—H2A | 120.3 | C12—C11—C10 | 122.88 (12) |
C1—C2—H2A | 120.3 | C12—C11—Cl1 | 116.73 (10) |
O2—C3—C2 | 124.90 (11) | C10—C11—Cl1 | 120.40 (9) |
O2—C3—C4 | 115.06 (11) | C11—C12—C13 | 118.09 (12) |
C2—C3—C4 | 120.04 (11) | C11—C12—H12A | 121.0 |
C5—C4—C3 | 119.77 (11) | C13—C12—H12A | 121.0 |
C5—C4—H4A | 120.1 | C12—C13—C14 | 121.49 (12) |
C3—C4—H4A | 120.1 | C12—C13—Cl2 | 119.03 (11) |
C4—C5—C6 | 121.34 (11) | C14—C13—Cl2 | 119.48 (11) |
C4—C5—H5A | 119.3 | C15—C14—C13 | 119.04 (12) |
C6—C5—H5A | 119.3 | C15—C14—H14A | 120.5 |
C1—C6—C5 | 118.10 (11) | C13—C14—H14A | 120.5 |
C1—C6—C7 | 123.30 (10) | C14—C15—C10 | 121.94 (12) |
C5—C6—C7 | 118.60 (10) | C14—C15—H15A | 119.0 |
O1—C7—C6 | 120.25 (11) | C10—C15—H15A | 119.0 |
O1—C7—C8 | 120.40 (11) | O2—C16—H16A | 109.5 |
C6—C7—C8 | 119.35 (10) | O2—C16—H16B | 109.5 |
C9—C8—C7 | 119.17 (11) | H16A—C16—H16B | 109.5 |
C9—C8—H8A | 120.4 | O2—C16—H16C | 109.5 |
C7—C8—H8A | 120.4 | H16A—C16—H16C | 109.5 |
C8—C9—C10 | 126.97 (11) | H16B—C16—H16C | 109.5 |
C6—C1—C2—C3 | −0.03 (18) | C6—C7—C8—C9 | −162.05 (12) |
C16—O2—C3—C2 | −3.65 (19) | C7—C8—C9—C10 | 179.98 (12) |
C16—O2—C3—C4 | 176.68 (12) | C8—C9—C10—C11 | −171.67 (13) |
C1—C2—C3—O2 | 179.96 (12) | C8—C9—C10—C15 | 8.5 (2) |
C1—C2—C3—C4 | −0.39 (19) | C15—C10—C11—C12 | 0.92 (19) |
O2—C3—C4—C5 | 179.99 (12) | C9—C10—C11—C12 | −178.91 (13) |
C2—C3—C4—C5 | 0.31 (19) | C15—C10—C11—Cl1 | −178.64 (10) |
C3—C4—C5—C6 | 0.2 (2) | C9—C10—C11—Cl1 | 1.53 (17) |
C2—C1—C6—C5 | 0.51 (18) | C10—C11—C12—C13 | 0.4 (2) |
C2—C1—C6—C7 | 179.57 (11) | Cl1—C11—C12—C13 | −179.98 (11) |
C4—C5—C6—C1 | −0.60 (18) | C11—C12—C13—C14 | −1.5 (2) |
C4—C5—C6—C7 | −179.70 (12) | C11—C12—C13—Cl2 | 178.17 (10) |
C1—C6—C7—O1 | −175.38 (12) | C12—C13—C14—C15 | 1.2 (2) |
C5—C6—C7—O1 | 3.67 (17) | Cl2—C13—C14—C15 | −178.50 (11) |
C1—C6—C7—C8 | 3.89 (17) | C13—C14—C15—C10 | 0.3 (2) |
C5—C6—C7—C8 | −177.05 (11) | C11—C10—C15—C14 | −1.27 (19) |
O1—C7—C8—C9 | 17.23 (18) | C9—C10—C15—C14 | 178.55 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1i | 0.93 | 2.47 | 3.2695 (15) | 143 |
C9—H9A···Cl1 | 0.93 | 2.61 | 3.0536 (11) | 109 |
C9—H9A···O1 | 0.93 | 2.44 | 2.7840 (15) | 101 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
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