Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006520/jh6037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006520/jh6037Isup2.hkl |
CCDC reference: 605106
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C15H12Cl2O2 | F(000) = 1216 |
Mr = 295.15 | Dx = 1.451 Mg m−3 |
Monoclinic, P21/c | Melting point: 374(375) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.2952 (14) Å | Cell parameters from 5943 reflections |
b = 11.5678 (10) Å | θ = 2.3–27.9° |
c = 14.6687 (12) Å | µ = 0.47 mm−1 |
β = 102.230 (1)° | T = 273 K |
V = 2702.3 (4) Å3 | Block, light-green |
Z = 8 | 0.54 × 0.44 × 0.34 mm |
Bruker SMART CCD area-detector diffractometer | 4449 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
φ and ω scans | h = −21→20 |
16721 measured reflections | k = −15→14 |
6171 independent reflections | l = −19→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0651P)2 + 1.271P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
6171 reflections | Δρmax = 0.46 e Å−3 |
437 parameters | Δρmin = −0.41 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0100 (10) |
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 | ||
Cl3 | 0.25441 (4) | 0.94861 (6) | 0.41165 (5) | 0.0611 (2) | |
Cl4 | 0.21452 (5) | 0.78455 (7) | 0.05536 (5) | 0.0677 (2) | |
Cl2 | 0.93200 (5) | 0.72977 (8) | 0.57212 (5) | 0.0727 (2) | |
Cl1 | 0.88389 (5) | 0.50777 (7) | 0.88542 (5) | 0.0745 (2) | |
C1 | 0.90905 (14) | 0.62182 (19) | 0.73055 (15) | 0.0433 (5) | |
C2 | 0.95900 (15) | 0.6963 (2) | 0.69037 (17) | 0.0478 (5) | |
C6 | 0.93872 (15) | 0.6005 (2) | 0.82568 (16) | 0.0495 (6) | |
C5 | 1.01105 (18) | 0.6505 (3) | 0.8767 (2) | 0.0614 (7) | |
C3 | 1.03130 (16) | 0.7467 (2) | 0.7406 (2) | 0.0583 (7) | |
C4 | 1.05665 (18) | 0.7234 (3) | 0.8335 (2) | 0.0653 (8) | |
C7 | 0.60033 (13) | 0.68364 (19) | 0.59255 (15) | 0.0420 (5) | |
C8 | 0.60720 (16) | 0.8032 (2) | 0.59746 (19) | 0.0526 (6) | |
C12 | 0.52106 (16) | 0.6345 (3) | 0.57056 (18) | 0.0556 (6) | |
C10 | 0.45781 (18) | 0.8210 (3) | 0.5587 (2) | 0.0682 (8) | |
C11 | 0.45038 (17) | 0.7027 (3) | 0.5534 (2) | 0.0666 (8) | |
C9 | 0.5358 (2) | 0.8703 (3) | 0.5804 (2) | 0.0676 (8) | |
C17 | 0.23189 (13) | 0.86710 (17) | 0.23234 (15) | 0.0389 (4) | |
C16 | 0.20872 (14) | 0.94800 (18) | 0.29301 (16) | 0.0437 (5) | |
C18 | 0.19059 (13) | 0.8782 (2) | 0.13941 (16) | 0.0447 (5) | |
C19 | 0.12999 (16) | 0.9614 (3) | 0.1085 (2) | 0.0587 (7) | |
C20 | 0.10881 (18) | 1.0370 (3) | 0.1715 (2) | 0.0655 (8) | |
C21 | 0.14789 (17) | 1.0314 (2) | 0.2636 (2) | 0.0572 (6) | |
C25 | 0.53958 (14) | 0.7414 (2) | 0.32460 (15) | 0.0440 (5) | |
C24 | 0.57187 (16) | 0.8527 (2) | 0.32941 (19) | 0.0527 (6) | |
C26 | 0.59525 (17) | 0.6493 (3) | 0.3477 (2) | 0.0596 (7) | |
C23 | 0.65711 (18) | 0.8715 (3) | 0.3575 (2) | 0.0677 (8) | |
C27 | 0.68029 (18) | 0.6690 (3) | 0.3761 (2) | 0.0723 (9) | |
C22 | 0.71102 (18) | 0.7800 (3) | 0.3815 (2) | 0.0710 (8) | |
C30 | 0.44832 (14) | 0.71587 (19) | 0.29520 (16) | 0.0438 (5) | |
C29 | 0.38532 (14) | 0.8136 (2) | 0.28530 (19) | 0.0435 (5) | |
C28 | 0.29524 (14) | 0.77119 (18) | 0.26312 (17) | 0.0424 (5) | |
C14 | 0.75970 (15) | 0.6571 (2) | 0.65023 (19) | 0.0492 (6) | |
C13 | 0.67505 (14) | 0.60741 (19) | 0.60843 (16) | 0.0450 (5) | |
C15 | 0.82778 (15) | 0.5696 (2) | 0.67793 (17) | 0.0477 (5) | |
O1 | 0.42389 (11) | 0.61682 (15) | 0.27974 (15) | 0.0662 (5) | |
O3 | 0.66778 (12) | 0.50563 (15) | 0.58650 (16) | 0.0714 (6) | |
O2 | 0.27356 (13) | 0.71289 (17) | 0.34007 (16) | 0.0643 (5) | |
O4 | 0.84486 (15) | 0.5037 (2) | 0.60308 (18) | 0.0874 (7) | |
H4 | 0.8020 | 0.4703 | 0.5767 | 0.131* | |
H8 | 0.6596 (17) | 0.840 (2) | 0.6078 (18) | 0.058 (7)* | |
H18 | 0.3950 (17) | 0.856 (3) | 0.343 (2) | 0.063 (8)* | |
H13 | 0.108 (2) | 0.962 (3) | 0.049 (2) | 0.073 (9)* | |
H19 | 0.3955 (16) | 0.858 (2) | 0.2358 (19) | 0.059 (8)* | |
H1 | 1.0246 (19) | 0.634 (3) | 0.936 (2) | 0.072 (9)* | |
H6 | 0.774 (2) | 0.710 (3) | 0.602 (2) | 0.080 (10)* | |
H3 | 1.0634 (19) | 0.792 (3) | 0.706 (2) | 0.072 (9)* | |
H7 | 0.7571 (18) | 0.707 (3) | 0.705 (2) | 0.072 (9)* | |
H15 | 0.1331 (19) | 1.079 (3) | 0.312 (2) | 0.072 (9)* | |
H2 | 1.104 (2) | 0.753 (3) | 0.866 (2) | 0.072 (9)* | |
H24 | 0.5726 (19) | 0.574 (3) | 0.346 (2) | 0.072 (9)* | |
H14 | 0.064 (2) | 1.087 (3) | 0.149 (2) | 0.081 (10)* | |
H17 | 0.2899 (15) | 0.715 (2) | 0.2125 (18) | 0.049 (7)* | |
H20 | 0.5366 (16) | 0.910 (2) | 0.3139 (17) | 0.049 (7)* | |
H23 | 0.716 (2) | 0.610 (3) | 0.390 (2) | 0.087 (10)* | |
H22 | 0.773 (2) | 0.792 (3) | 0.397 (2) | 0.084 (10)* | |
H11 | 0.399 (2) | 0.674 (3) | 0.539 (2) | 0.068 (9)* | |
H10 | 0.409 (2) | 0.863 (3) | 0.547 (2) | 0.077 (9)* | |
H5 | 0.8178 (18) | 0.492 (3) | 0.717 (2) | 0.074 (9)* | |
H12 | 0.5172 (19) | 0.549 (3) | 0.568 (2) | 0.072 (9)* | |
H9 | 0.543 (2) | 0.949 (3) | 0.583 (2) | 0.088 (11)* | |
H21 | 0.6781 (19) | 0.948 (3) | 0.361 (2) | 0.073 (9)* | |
H16 | 0.308 (2) | 0.667 (4) | 0.350 (3) | 0.105 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl3 | 0.0694 (4) | 0.0571 (4) | 0.0550 (4) | −0.0039 (3) | 0.0089 (3) | −0.0089 (3) |
Cl4 | 0.0680 (4) | 0.0818 (5) | 0.0509 (4) | 0.0107 (4) | 0.0068 (3) | −0.0097 (3) |
Cl2 | 0.0712 (5) | 0.0918 (6) | 0.0569 (4) | −0.0006 (4) | 0.0173 (3) | 0.0207 (4) |
Cl1 | 0.0817 (5) | 0.0834 (5) | 0.0625 (4) | 0.0180 (4) | 0.0244 (4) | 0.0260 (4) |
C1 | 0.0425 (11) | 0.0414 (11) | 0.0450 (12) | 0.0111 (9) | 0.0070 (9) | −0.0014 (9) |
C2 | 0.0463 (12) | 0.0475 (13) | 0.0496 (13) | 0.0094 (10) | 0.0106 (10) | 0.0019 (10) |
C6 | 0.0508 (13) | 0.0517 (13) | 0.0459 (13) | 0.0189 (11) | 0.0102 (10) | 0.0018 (10) |
C5 | 0.0564 (16) | 0.0742 (19) | 0.0476 (15) | 0.0241 (14) | −0.0023 (12) | −0.0064 (13) |
C3 | 0.0445 (13) | 0.0523 (14) | 0.0780 (19) | 0.0050 (11) | 0.0125 (13) | −0.0034 (13) |
C4 | 0.0461 (15) | 0.0671 (18) | 0.075 (2) | 0.0103 (13) | −0.0048 (14) | −0.0176 (15) |
C7 | 0.0409 (11) | 0.0430 (12) | 0.0405 (11) | −0.0027 (9) | 0.0053 (9) | 0.0021 (9) |
C8 | 0.0469 (13) | 0.0427 (13) | 0.0661 (16) | −0.0011 (10) | 0.0069 (11) | −0.0014 (11) |
C12 | 0.0484 (14) | 0.0598 (16) | 0.0563 (15) | −0.0109 (12) | 0.0055 (11) | −0.0012 (12) |
C10 | 0.0503 (15) | 0.091 (2) | 0.0591 (17) | 0.0223 (15) | 0.0021 (12) | −0.0047 (15) |
C11 | 0.0405 (14) | 0.096 (2) | 0.0604 (17) | −0.0057 (14) | 0.0043 (12) | −0.0071 (15) |
C9 | 0.0667 (18) | 0.0530 (17) | 0.078 (2) | 0.0167 (14) | 0.0041 (15) | −0.0046 (14) |
C17 | 0.0349 (10) | 0.0308 (10) | 0.0493 (12) | −0.0024 (8) | 0.0050 (9) | 0.0022 (8) |
C16 | 0.0442 (11) | 0.0342 (11) | 0.0518 (13) | −0.0020 (9) | 0.0084 (10) | 0.0018 (9) |
C18 | 0.0378 (11) | 0.0473 (12) | 0.0488 (12) | −0.0010 (9) | 0.0084 (9) | 0.0053 (10) |
C19 | 0.0464 (14) | 0.0690 (17) | 0.0579 (16) | 0.0096 (12) | 0.0049 (12) | 0.0205 (14) |
C20 | 0.0561 (15) | 0.0552 (16) | 0.086 (2) | 0.0211 (13) | 0.0161 (14) | 0.0209 (15) |
C21 | 0.0595 (15) | 0.0392 (13) | 0.0756 (18) | 0.0104 (11) | 0.0205 (14) | 0.0030 (12) |
C25 | 0.0444 (12) | 0.0479 (13) | 0.0418 (12) | 0.0086 (9) | 0.0138 (9) | 0.0051 (9) |
C24 | 0.0447 (13) | 0.0525 (14) | 0.0611 (15) | 0.0055 (11) | 0.0116 (11) | 0.0016 (12) |
C26 | 0.0550 (15) | 0.0568 (16) | 0.0697 (17) | 0.0148 (12) | 0.0190 (13) | 0.0151 (13) |
C23 | 0.0519 (15) | 0.075 (2) | 0.075 (2) | −0.0073 (14) | 0.0122 (14) | −0.0014 (16) |
C27 | 0.0507 (16) | 0.090 (2) | 0.079 (2) | 0.0281 (16) | 0.0183 (14) | 0.0283 (17) |
C22 | 0.0421 (14) | 0.101 (3) | 0.0696 (19) | 0.0051 (15) | 0.0111 (13) | 0.0157 (17) |
C30 | 0.0466 (12) | 0.0378 (11) | 0.0480 (12) | 0.0050 (9) | 0.0125 (10) | 0.0024 (9) |
C29 | 0.0400 (11) | 0.0364 (11) | 0.0537 (14) | 0.0019 (9) | 0.0091 (10) | 0.0015 (10) |
C28 | 0.0412 (11) | 0.0325 (11) | 0.0513 (13) | 0.0025 (8) | 0.0048 (9) | 0.0008 (9) |
C14 | 0.0433 (12) | 0.0468 (13) | 0.0560 (14) | 0.0027 (10) | 0.0068 (11) | −0.0069 (11) |
C13 | 0.0489 (12) | 0.0370 (11) | 0.0470 (12) | −0.0028 (9) | 0.0058 (10) | 0.0056 (9) |
C15 | 0.0476 (12) | 0.0436 (12) | 0.0495 (13) | 0.0033 (10) | 0.0049 (10) | −0.0007 (10) |
O1 | 0.0571 (11) | 0.0374 (9) | 0.1043 (16) | 0.0047 (8) | 0.0174 (10) | −0.0032 (9) |
O3 | 0.0656 (12) | 0.0328 (9) | 0.1045 (16) | −0.0008 (8) | −0.0074 (11) | 0.0023 (9) |
O2 | 0.0589 (11) | 0.0468 (10) | 0.0916 (15) | 0.0102 (9) | 0.0256 (10) | 0.0279 (10) |
O4 | 0.0803 (15) | 0.0850 (16) | 0.0959 (17) | 0.0070 (12) | 0.0159 (13) | −0.0357 (13) |
Cl3—C16 | 1.742 (2) | C19—H13 | 0.87 (3) |
Cl4—C18 | 1.746 (2) | C20—C21 | 1.367 (4) |
Cl2—C2 | 1.740 (2) | C20—H14 | 0.93 (3) |
Cl1—C6 | 1.746 (3) | C21—H15 | 0.97 (3) |
C1—C2 | 1.399 (3) | C25—C24 | 1.387 (4) |
C1—C6 | 1.399 (3) | C25—C26 | 1.394 (3) |
C1—C15 | 1.511 (3) | C25—C30 | 1.488 (3) |
C2—C3 | 1.379 (4) | C24—C23 | 1.380 (4) |
C6—C5 | 1.381 (4) | C24—H20 | 0.88 (3) |
C5—C4 | 1.365 (5) | C26—C27 | 1.379 (4) |
C5—H1 | 0.87 (3) | C26—H24 | 0.95 (3) |
C3—C4 | 1.365 (4) | C23—C22 | 1.373 (5) |
C3—H3 | 0.96 (3) | C23—H21 | 0.94 (3) |
C4—H2 | 0.88 (3) | C27—C22 | 1.374 (5) |
C7—C12 | 1.385 (3) | C27—H23 | 0.89 (4) |
C7—C8 | 1.388 (3) | C22—H22 | 1.00 (3) |
C7—C13 | 1.481 (3) | C30—O1 | 1.218 (3) |
C8—C9 | 1.377 (4) | C30—C29 | 1.513 (3) |
C8—H8 | 0.93 (3) | C29—C28 | 1.516 (3) |
C12—C11 | 1.375 (4) | C29—H18 | 0.97 (3) |
C12—H12 | 0.99 (3) | C29—H19 | 0.93 (3) |
C10—C9 | 1.367 (5) | C28—O2 | 1.422 (3) |
C10—C11 | 1.374 (5) | C28—H17 | 0.97 (3) |
C10—H10 | 0.92 (3) | C14—C15 | 1.493 (3) |
C11—H11 | 0.89 (3) | C14—C13 | 1.500 (3) |
C9—H9 | 0.92 (4) | C14—H6 | 1.00 (3) |
C17—C18 | 1.392 (3) | C14—H7 | 1.01 (3) |
C17—C16 | 1.397 (3) | C13—O3 | 1.220 (3) |
C17—C28 | 1.517 (3) | C15—O4 | 1.412 (3) |
C16—C21 | 1.385 (3) | C15—H5 | 1.10 (3) |
C18—C19 | 1.384 (3) | O2—H16 | 0.77 (4) |
C19—C20 | 1.369 (4) | O4—H4 | 0.8200 |
C2—C1—C6 | 114.8 (2) | C20—C21—H15 | 124.3 (18) |
C2—C1—C15 | 123.8 (2) | C16—C21—H15 | 115.9 (18) |
C6—C1—C15 | 121.3 (2) | C24—C25—C26 | 118.5 (2) |
C3—C2—C1 | 122.9 (2) | C24—C25—C30 | 123.0 (2) |
C3—C2—Cl2 | 116.4 (2) | C26—C25—C30 | 118.6 (2) |
C1—C2—Cl2 | 120.68 (19) | C23—C24—C25 | 120.6 (3) |
C5—C6—C1 | 122.8 (3) | C23—C24—H20 | 121.2 (17) |
C5—C6—Cl1 | 117.0 (2) | C25—C24—H20 | 118.2 (17) |
C1—C6—Cl1 | 120.22 (19) | C27—C26—C25 | 120.5 (3) |
C4—C5—C6 | 119.6 (3) | C27—C26—H24 | 121.5 (19) |
C4—C5—H1 | 123 (2) | C25—C26—H24 | 117.9 (19) |
C6—C5—H1 | 117 (2) | C22—C23—C24 | 120.2 (3) |
C4—C3—C2 | 119.6 (3) | C22—C23—H21 | 120.1 (19) |
C4—C3—H3 | 123.7 (19) | C24—C23—H21 | 119.7 (19) |
C2—C3—H3 | 116.5 (19) | C22—C27—C26 | 120.2 (3) |
C5—C4—C3 | 120.4 (3) | C22—C27—H23 | 119 (2) |
C5—C4—H2 | 120 (2) | C26—C27—H23 | 121 (2) |
C3—C4—H2 | 120 (2) | C23—C22—C27 | 120.0 (3) |
C12—C7—C8 | 118.8 (2) | C23—C22—H22 | 121 (2) |
C12—C7—C13 | 119.1 (2) | C27—C22—H22 | 119 (2) |
C8—C7—C13 | 122.0 (2) | O1—C30—C25 | 120.5 (2) |
C9—C8—C7 | 119.8 (3) | O1—C30—C29 | 119.8 (2) |
C9—C8—H8 | 118.9 (17) | C25—C30—C29 | 119.71 (19) |
C7—C8—H8 | 121.2 (17) | C30—C29—C28 | 112.64 (19) |
C11—C12—C7 | 120.7 (3) | C30—C29—H18 | 108.3 (17) |
C11—C12—H12 | 121.5 (18) | C28—C29—H18 | 108.9 (16) |
C7—C12—H12 | 117.8 (18) | C30—C29—H19 | 104.9 (17) |
C9—C10—C11 | 119.7 (3) | C28—C29—H19 | 109.6 (16) |
C9—C10—H10 | 123 (2) | H18—C29—H19 | 113 (2) |
C11—C10—H10 | 117 (2) | O2—C28—C29 | 112.0 (2) |
C10—C11—C12 | 120.1 (3) | O2—C28—C17 | 108.37 (18) |
C10—C11—H11 | 117 (2) | C29—C28—C17 | 113.19 (18) |
C12—C11—H11 | 123 (2) | O2—C28—H17 | 107.0 (15) |
C10—C9—C8 | 121.0 (3) | C29—C28—H17 | 107.7 (15) |
C10—C9—H9 | 122 (2) | C17—C28—H17 | 108.2 (15) |
C8—C9—H9 | 117 (2) | C15—C14—C13 | 114.7 (2) |
C18—C17—C16 | 115.0 (2) | C15—C14—H6 | 109.9 (19) |
C18—C17—C28 | 121.1 (2) | C13—C14—H6 | 105.9 (19) |
C16—C17—C28 | 124.0 (2) | C15—C14—H7 | 109.2 (17) |
C21—C16—C17 | 122.7 (2) | C13—C14—H7 | 111.0 (17) |
C21—C16—Cl3 | 115.78 (19) | H6—C14—H7 | 106 (3) |
C17—C16—Cl3 | 121.53 (17) | O3—C13—C7 | 120.2 (2) |
C19—C18—C17 | 123.2 (2) | O3—C13—C14 | 120.5 (2) |
C19—C18—Cl4 | 116.8 (2) | C7—C13—C14 | 119.4 (2) |
C17—C18—Cl4 | 120.01 (17) | O4—C15—C14 | 114.3 (2) |
C20—C19—C18 | 119.2 (3) | O4—C15—C1 | 108.5 (2) |
C20—C19—H13 | 124 (2) | C14—C15—C1 | 112.9 (2) |
C18—C19—H13 | 117 (2) | O4—C15—H5 | 92.2 (16) |
C21—C20—C19 | 120.3 (3) | C14—C15—H5 | 121.0 (16) |
C21—C20—H14 | 123 (2) | C1—C15—H5 | 105.7 (16) |
C19—C20—H14 | 117 (2) | C28—O2—H16 | 101 (3) |
C20—C21—C16 | 119.6 (3) | C15—O4—H4 | 109.5 |
C6—C1—C2—C3 | −1.0 (3) | C17—C16—C21—C20 | −0.7 (4) |
C15—C1—C2—C3 | 177.4 (2) | Cl3—C16—C21—C20 | 180.0 (2) |
C6—C1—C2—Cl2 | 178.83 (16) | C26—C25—C24—C23 | −0.7 (4) |
C15—C1—C2—Cl2 | −2.8 (3) | C30—C25—C24—C23 | 179.7 (2) |
C2—C1—C6—C5 | 0.9 (3) | C24—C25—C26—C27 | 1.0 (4) |
C15—C1—C6—C5 | −177.4 (2) | C30—C25—C26—C27 | −179.4 (3) |
C2—C1—C6—Cl1 | −179.19 (17) | C25—C24—C23—C22 | −0.3 (4) |
C15—C1—C6—Cl1 | 2.4 (3) | C25—C26—C27—C22 | −0.3 (5) |
C1—C6—C5—C4 | −0.4 (4) | C24—C23—C22—C27 | 1.0 (5) |
Cl1—C6—C5—C4 | 179.8 (2) | C26—C27—C22—C23 | −0.7 (5) |
C1—C2—C3—C4 | 0.4 (4) | C24—C25—C30—O1 | 169.9 (2) |
Cl2—C2—C3—C4 | −179.4 (2) | C26—C25—C30—O1 | −9.6 (3) |
C6—C5—C4—C3 | −0.3 (4) | C24—C25—C30—C29 | −10.7 (3) |
C2—C3—C4—C5 | 0.2 (4) | C26—C25—C30—C29 | 169.8 (2) |
C12—C7—C8—C9 | −0.1 (4) | O1—C30—C29—C28 | 4.4 (3) |
C13—C7—C8—C9 | 178.8 (2) | C25—C30—C29—C28 | −175.0 (2) |
C8—C7—C12—C11 | 0.3 (4) | C30—C29—C28—O2 | 69.7 (3) |
C13—C7—C12—C11 | −178.6 (2) | C30—C29—C28—C17 | −167.4 (2) |
C9—C10—C11—C12 | 0.4 (5) | C18—C17—C28—O2 | −128.7 (2) |
C7—C12—C11—C10 | −0.5 (4) | C16—C17—C28—O2 | 49.6 (3) |
C11—C10—C9—C8 | −0.2 (5) | C18—C17—C28—C29 | 106.4 (2) |
C7—C8—C9—C10 | 0.0 (5) | C16—C17—C28—C29 | −75.3 (3) |
C18—C17—C16—C21 | 1.4 (3) | C12—C7—C13—O3 | 12.9 (4) |
C28—C17—C16—C21 | −177.0 (2) | C8—C7—C13—O3 | −166.0 (3) |
C18—C17—C16—Cl3 | −179.34 (16) | C12—C7—C13—C14 | −168.1 (2) |
C28—C17—C16—Cl3 | 2.3 (3) | C8—C7—C13—C14 | 13.0 (3) |
C16—C17—C18—C19 | −1.0 (3) | C15—C14—C13—O3 | −10.9 (4) |
C28—C17—C18—C19 | 177.4 (2) | C15—C14—C13—C7 | 170.1 (2) |
C16—C17—C18—Cl4 | 178.90 (16) | C13—C14—C15—O4 | 62.6 (3) |
C28—C17—C18—Cl4 | −2.7 (3) | C13—C14—C15—C1 | −172.7 (2) |
C17—C18—C19—C20 | 0.0 (4) | C2—C1—C15—O4 | 59.5 (3) |
Cl4—C18—C19—C20 | −180.0 (2) | C6—C1—C15—O4 | −122.3 (2) |
C18—C19—C20—C21 | 0.8 (4) | C2—C1—C15—C14 | −68.3 (3) |
C19—C20—C21—C16 | −0.5 (4) | C6—C1—C15—C14 | 110.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3 | 0.82 | 2.26 | 2.844 (3) | 129 |
O2—H16···O1 | 0.77 (4) | 2.41 (4) | 2.990 (3) | 134 (4) |
O4—H4···Cl4i | 0.82 | 2.87 | 3.437 (2) | 128 |
O2—H16···O3ii | 0.77 (4) | 2.20 (4) | 2.833 (3) | 141 (4) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1. |