Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043674/hb2167sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043674/hb2167Isup2.hkl |
CCDC reference: 627684
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.
C24H19Cl4NO7 | F(000) = 1176 |
Mr = 575.20 | Dx = 1.515 Mg m−3 |
Orthorhombic, P212121 | Melting point: 465 K |
Hall symbol: P 2ac 2 ab | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0242 (15) Å | µ = 0.52 mm−1 |
b = 17.487 (3) Å | T = 294 K |
c = 17.969 (3) Å | Prism, colourless |
V = 2521.3 (8) Å3 | 0.30 × 0.26 × 0.20 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 5119 independent reflections |
Radiation source: fine-focus sealed tube | 3373 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 26.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −9→10 |
Tmin = 0.861, Tmax = 0.904 | k = −21→12 |
14278 measured reflections | l = −21→22 |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0363P)2 + 0.6629P] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.006 |
5119 reflections | Δρmax = 0.19 e Å−3 |
326 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2201 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.08 (7) |
Experimental. 1H NMR (300 MHz, CDCl3): δ 7.50–7.26 (m, 5H), 5.72 (d, 1H, J = 8.3 Hz), 5.50 (s, 1H), 5.30–5.19 (m, 2H), 5.14–5.07 (m, 1H), 4.62–4.55 (m, 1H), 4.39–4.16 (m, 3H), 4.06–4.00 (m, 1H), 3.86–3.78 (m, 1H), 3.61–3.58 (m, 2H), 2.87 (d, 1H, J = 3.7 Hz); 13C NMR (75 MHz, CDCl3): δ140.26, 136.81, 133.25, 129.29, 128.30, 127.17, 126.09, 117.92 (CH2), 101.77, 97.64, 82.00, 70.13 (CH2), 68.60 (CH2), 68.16, 66.34, 57.08; ESI–MS: m/z 596.1 (M+ + Na) |
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 | 0.70633 (12) | 0.56105 (5) | −0.03722 (5) | 0.0606 (2) | |
Cl2 | 0.84621 (17) | 0.70527 (5) | 0.04295 (7) | 0.0977 (4) | |
Cl3 | 0.98845 (14) | 0.69431 (6) | 0.20248 (7) | 0.0872 (4) | |
Cl4 | 0.99076 (18) | 0.53677 (7) | 0.28546 (6) | 0.1006 (4) | |
O1 | 0.9094 (3) | 0.36914 (15) | 0.23891 (13) | 0.0670 (7) | |
O2 | 0.6901 (3) | 0.38582 (11) | 0.00436 (11) | 0.0450 (5) | |
O3 | 1.0009 (3) | 0.23551 (12) | 0.06678 (13) | 0.0520 (6) | |
H3 | 1.0435 | 0.1967 | 0.0497 | 0.078* | |
O4 | 0.5284 (3) | 0.30222 (13) | 0.20587 (12) | 0.0519 (6) | |
O5 | 0.5343 (3) | 0.18510 (11) | 0.15057 (11) | 0.0453 (5) | |
O6 | 0.5885 (3) | 0.01967 (12) | 0.03117 (12) | 0.0496 (6) | |
O7 | 0.8106 (2) | 0.10317 (11) | 0.01122 (11) | 0.0447 (5) | |
N1 | 0.7923 (3) | 0.35790 (13) | 0.12169 (13) | 0.0381 (6) | |
C1 | 0.8635 (4) | 0.39799 (19) | 0.18217 (19) | 0.0476 (8) | |
C2 | 0.8658 (4) | 0.47955 (18) | 0.15820 (18) | 0.0438 (8) | |
C3 | 0.9210 (4) | 0.5436 (2) | 0.1951 (2) | 0.0568 (9) | |
C4 | 0.9153 (4) | 0.6138 (2) | 0.1584 (2) | 0.0578 (10) | |
C5 | 0.8506 (4) | 0.61918 (19) | 0.0868 (2) | 0.0554 (9) | |
C6 | 0.7903 (4) | 0.55352 (18) | 0.05008 (18) | 0.0468 (8) | |
C7 | 0.8014 (4) | 0.48449 (17) | 0.08634 (17) | 0.0406 (7) | |
C8 | 0.7519 (4) | 0.40579 (17) | 0.06269 (17) | 0.0378 (7) | |
C9 | 0.7547 (4) | 0.27618 (16) | 0.12750 (16) | 0.0381 (7) | |
H9 | 0.8106 | 0.2581 | 0.1727 | 0.046* | |
C10 | 0.5673 (4) | 0.26406 (18) | 0.14048 (17) | 0.0420 (8) | |
H10 | 0.5024 | 0.2845 | 0.0988 | 0.050* | |
C11 | 0.5791 (4) | 0.14304 (17) | 0.08593 (17) | 0.0391 (7) | |
H11 | 0.5221 | 0.1642 | 0.0423 | 0.047* | |
C12 | 0.7671 (4) | 0.14780 (16) | 0.07512 (16) | 0.0365 (7) | |
H12 | 0.8226 | 0.1265 | 0.1190 | 0.044* | |
C13 | 0.8239 (4) | 0.22870 (15) | 0.06413 (16) | 0.0370 (7) | |
H13 | 0.7822 | 0.2482 | 0.0165 | 0.044* | |
C14 | 0.3563 (4) | 0.3014 (2) | 0.2255 (2) | 0.0628 (10) | |
H14A | 0.3167 | 0.2491 | 0.2290 | 0.075* | |
H14B | 0.2913 | 0.3277 | 0.1879 | 0.075* | |
C15 | 0.3375 (6) | 0.3403 (2) | 0.2983 (2) | 0.0730 (12) | |
H15 | 0.2294 | 0.3491 | 0.3149 | 0.088* | |
C16 | 0.4553 (7) | 0.3630 (3) | 0.3403 (2) | 0.0928 (15) | |
H16A | 0.5656 | 0.3555 | 0.3261 | 0.111* | |
H16B | 0.4312 | 0.3870 | 0.3852 | 0.111* | |
C17 | 0.5326 (4) | 0.06032 (17) | 0.09557 (17) | 0.0495 (8) | |
H17A | 0.5850 | 0.0397 | 0.1399 | 0.059* | |
H17B | 0.4128 | 0.0553 | 0.1008 | 0.059* | |
C18 | 0.7619 (4) | 0.02616 (17) | 0.02053 (18) | 0.0449 (8) | |
H18 | 0.8190 | 0.0052 | 0.0642 | 0.054* | |
C19 | 0.8114 (4) | −0.01946 (18) | −0.04691 (19) | 0.0472 (8) | |
C20 | 0.8116 (5) | −0.09824 (19) | −0.0437 (2) | 0.0693 (11) | |
H20 | 0.7788 | −0.1228 | −0.0001 | 0.083* | |
C21 | 0.8599 (6) | −0.1408 (2) | −0.1043 (3) | 0.0845 (14) | |
H21 | 0.8611 | −0.1939 | −0.1012 | 0.101* | |
C22 | 0.9059 (5) | −0.1061 (3) | −0.1690 (2) | 0.0812 (13) | |
H22 | 0.9363 | −0.1352 | −0.2102 | 0.097* | |
C23 | 0.9069 (6) | −0.0283 (3) | −0.1726 (2) | 0.0858 (14) | |
H23 | 0.9400 | −0.0041 | −0.2162 | 0.103* | |
C24 | 0.8592 (5) | 0.0148 (2) | −0.1120 (2) | 0.0703 (12) | |
H24 | 0.8594 | 0.0679 | −0.1155 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0703 (6) | 0.0482 (5) | 0.0634 (5) | 0.0099 (4) | 0.0025 (5) | 0.0084 (5) |
Cl2 | 0.1414 (11) | 0.0334 (5) | 0.1183 (10) | −0.0014 (6) | 0.0072 (9) | 0.0016 (6) |
Cl3 | 0.0854 (7) | 0.0525 (6) | 0.1237 (9) | −0.0084 (6) | −0.0022 (7) | −0.0420 (6) |
Cl4 | 0.1399 (11) | 0.0861 (8) | 0.0757 (7) | −0.0250 (8) | −0.0404 (8) | −0.0244 (6) |
O1 | 0.0887 (19) | 0.0611 (16) | 0.0511 (15) | −0.0077 (15) | −0.0264 (14) | 0.0035 (14) |
O2 | 0.0552 (14) | 0.0384 (12) | 0.0414 (12) | −0.0032 (11) | −0.0069 (11) | −0.0045 (10) |
O3 | 0.0387 (12) | 0.0428 (12) | 0.0744 (15) | −0.0044 (11) | 0.0070 (12) | −0.0101 (12) |
O4 | 0.0503 (14) | 0.0567 (14) | 0.0485 (13) | −0.0043 (12) | 0.0094 (11) | −0.0127 (12) |
O5 | 0.0524 (13) | 0.0412 (12) | 0.0424 (12) | −0.0084 (11) | 0.0087 (10) | 0.0014 (10) |
O6 | 0.0558 (14) | 0.0413 (12) | 0.0517 (14) | −0.0144 (11) | −0.0024 (12) | −0.0041 (11) |
O7 | 0.0472 (13) | 0.0353 (11) | 0.0517 (12) | −0.0048 (10) | 0.0017 (10) | −0.0052 (10) |
N1 | 0.0436 (15) | 0.0339 (13) | 0.0369 (13) | −0.0050 (12) | −0.0020 (12) | −0.0043 (12) |
C1 | 0.0490 (19) | 0.046 (2) | 0.048 (2) | −0.0086 (17) | −0.0044 (16) | −0.0067 (17) |
C2 | 0.0409 (18) | 0.0416 (18) | 0.049 (2) | −0.0040 (15) | −0.0030 (15) | −0.0096 (16) |
C3 | 0.058 (2) | 0.048 (2) | 0.065 (2) | −0.0072 (17) | −0.0070 (19) | −0.0184 (19) |
C4 | 0.051 (2) | 0.041 (2) | 0.081 (3) | −0.0049 (17) | 0.005 (2) | −0.023 (2) |
C5 | 0.054 (2) | 0.0357 (18) | 0.077 (3) | 0.0010 (16) | 0.0102 (19) | −0.0054 (18) |
C6 | 0.0475 (18) | 0.0381 (17) | 0.0546 (19) | 0.0038 (15) | 0.0080 (17) | −0.0041 (17) |
C7 | 0.0386 (17) | 0.0351 (17) | 0.0480 (19) | −0.0021 (15) | 0.0039 (15) | −0.0061 (15) |
C8 | 0.0358 (17) | 0.0339 (16) | 0.0438 (18) | −0.0002 (14) | 0.0042 (15) | −0.0029 (15) |
C9 | 0.0415 (17) | 0.0352 (16) | 0.0377 (16) | −0.0023 (14) | −0.0017 (14) | 0.0031 (14) |
C10 | 0.0472 (19) | 0.0397 (17) | 0.0391 (17) | −0.0036 (15) | 0.0008 (15) | −0.0011 (15) |
C11 | 0.0412 (17) | 0.0391 (17) | 0.0371 (17) | −0.0025 (15) | −0.0011 (14) | 0.0034 (15) |
C12 | 0.0425 (18) | 0.0340 (16) | 0.0329 (16) | −0.0022 (14) | −0.0027 (14) | 0.0017 (14) |
C13 | 0.0380 (17) | 0.0330 (15) | 0.0401 (16) | −0.0010 (14) | −0.0033 (14) | 0.0028 (14) |
C14 | 0.053 (2) | 0.068 (2) | 0.067 (2) | −0.007 (2) | 0.0187 (19) | −0.008 (2) |
C15 | 0.078 (3) | 0.064 (3) | 0.078 (3) | −0.007 (2) | 0.033 (3) | −0.014 (2) |
C16 | 0.108 (4) | 0.092 (3) | 0.078 (3) | −0.007 (3) | 0.025 (3) | −0.032 (3) |
C17 | 0.056 (2) | 0.0461 (18) | 0.0461 (18) | −0.0161 (18) | 0.0043 (16) | 0.0025 (17) |
C18 | 0.050 (2) | 0.0359 (16) | 0.0484 (19) | −0.0041 (15) | −0.0080 (16) | 0.0013 (15) |
C19 | 0.052 (2) | 0.0402 (17) | 0.050 (2) | −0.0034 (16) | −0.0095 (17) | −0.0060 (16) |
C20 | 0.105 (3) | 0.042 (2) | 0.060 (2) | −0.003 (2) | −0.003 (2) | −0.010 (2) |
C21 | 0.112 (4) | 0.052 (2) | 0.089 (3) | 0.007 (3) | −0.008 (3) | −0.023 (3) |
C22 | 0.089 (3) | 0.092 (4) | 0.062 (3) | −0.004 (3) | 0.000 (2) | −0.032 (3) |
C23 | 0.122 (4) | 0.083 (3) | 0.052 (2) | −0.012 (3) | −0.001 (3) | −0.011 (2) |
C24 | 0.108 (4) | 0.052 (2) | 0.050 (2) | −0.006 (2) | −0.004 (2) | −0.0023 (19) |
Cl1—C6 | 1.712 (3) | C10—H10 | 0.9800 |
Cl2—C5 | 1.700 (4) | C11—C17 | 1.504 (4) |
Cl3—C4 | 1.719 (3) | C11—C12 | 1.523 (4) |
Cl4—C3 | 1.722 (4) | C11—H11 | 0.9800 |
O1—C1 | 1.196 (4) | C12—C13 | 1.499 (4) |
O2—C8 | 1.211 (3) | C12—H12 | 0.9800 |
O3—C13 | 1.426 (3) | C13—H13 | 0.9800 |
O3—H3 | 0.8200 | C14—C15 | 1.483 (5) |
O4—C10 | 1.387 (4) | C14—H14A | 0.9700 |
O4—C14 | 1.426 (4) | C14—H14B | 0.9700 |
O5—C10 | 1.417 (4) | C15—C16 | 1.273 (6) |
O5—C11 | 1.421 (4) | C15—H15 | 0.9300 |
O6—C18 | 1.409 (4) | C16—H16A | 0.9300 |
O6—C17 | 1.430 (4) | C16—H16B | 0.9300 |
O7—C18 | 1.412 (3) | C17—H17A | 0.9700 |
O7—C12 | 1.432 (3) | C17—H17B | 0.9700 |
N1—C8 | 1.389 (4) | C18—C19 | 1.504 (4) |
N1—C1 | 1.414 (4) | C18—H18 | 0.9800 |
N1—C9 | 1.464 (4) | C19—C24 | 1.370 (5) |
C1—C2 | 1.490 (5) | C19—C20 | 1.379 (4) |
C2—C3 | 1.375 (4) | C20—C21 | 1.376 (5) |
C2—C7 | 1.393 (4) | C20—H20 | 0.9300 |
C3—C4 | 1.394 (5) | C21—C22 | 1.361 (6) |
C4—C5 | 1.391 (5) | C21—H21 | 0.9300 |
C5—C6 | 1.410 (4) | C22—C23 | 1.363 (6) |
C6—C7 | 1.374 (4) | C22—H22 | 0.9300 |
C7—C8 | 1.494 (4) | C23—C24 | 1.377 (5) |
C9—C13 | 1.515 (4) | C23—H23 | 0.9300 |
C9—C10 | 1.536 (4) | C24—H24 | 0.9300 |
C9—H9 | 0.9800 | ||
C13—O3—H3 | 109.5 | C13—C12—C11 | 111.7 (3) |
C10—O4—C14 | 115.0 (2) | O7—C12—H12 | 109.1 |
C10—O5—C11 | 110.6 (2) | C13—C12—H12 | 109.1 |
C18—O6—C17 | 112.3 (2) | C11—C12—H12 | 109.1 |
C18—O7—C12 | 110.9 (2) | O3—C13—C12 | 112.2 (2) |
C8—N1—C1 | 112.4 (2) | O3—C13—C9 | 107.1 (2) |
C8—N1—C9 | 126.5 (2) | C12—C13—C9 | 107.9 (2) |
C1—N1—C9 | 120.8 (2) | O3—C13—H13 | 109.9 |
O1—C1—N1 | 124.8 (3) | C12—C13—H13 | 109.9 |
O1—C1—C2 | 130.3 (3) | C9—C13—H13 | 109.9 |
N1—C1—C2 | 104.9 (3) | O4—C14—C15 | 108.2 (3) |
C3—C2—C7 | 121.0 (3) | O4—C14—H14A | 110.1 |
C3—C2—C1 | 130.1 (3) | C15—C14—H14A | 110.1 |
C7—C2—C1 | 108.8 (3) | O4—C14—H14B | 110.1 |
C2—C3—C4 | 118.6 (3) | C15—C14—H14B | 110.1 |
C2—C3—Cl4 | 120.2 (3) | H14A—C14—H14B | 108.4 |
C4—C3—Cl4 | 121.1 (3) | C16—C15—C14 | 126.2 (4) |
C5—C4—C3 | 120.6 (3) | C16—C15—H15 | 116.9 |
C5—C4—Cl3 | 119.9 (3) | C14—C15—H15 | 116.9 |
C3—C4—Cl3 | 119.5 (3) | C15—C16—H16A | 120.0 |
C4—C5—C6 | 120.4 (3) | C15—C16—H16B | 120.0 |
C4—C5—Cl2 | 119.8 (3) | H16A—C16—H16B | 120.0 |
C6—C5—Cl2 | 119.8 (3) | O6—C17—C11 | 107.9 (2) |
C7—C6—C5 | 118.1 (3) | O6—C17—H17A | 110.1 |
C7—C6—Cl1 | 121.8 (2) | C11—C17—H17A | 110.1 |
C5—C6—Cl1 | 120.1 (3) | O6—C17—H17B | 110.1 |
C6—C7—C2 | 121.2 (3) | C11—C17—H17B | 110.1 |
C6—C7—C8 | 131.1 (3) | H17A—C17—H17B | 108.4 |
C2—C7—C8 | 107.7 (3) | O6—C18—O7 | 111.5 (3) |
O2—C8—N1 | 125.6 (3) | O6—C18—C19 | 109.1 (2) |
O2—C8—C7 | 128.4 (3) | O7—C18—C19 | 109.7 (3) |
N1—C8—C7 | 106.0 (2) | O6—C18—H18 | 108.8 |
N1—C9—C13 | 113.9 (2) | O7—C18—H18 | 108.8 |
N1—C9—C10 | 110.3 (2) | C19—C18—H18 | 108.8 |
C13—C9—C10 | 113.4 (2) | C24—C19—C20 | 118.3 (3) |
N1—C9—H9 | 106.2 | C24—C19—C18 | 122.0 (3) |
C13—C9—H9 | 106.2 | C20—C19—C18 | 119.7 (3) |
C10—C9—H9 | 106.2 | C21—C20—C19 | 120.5 (4) |
O4—C10—O5 | 108.6 (2) | C21—C20—H20 | 119.8 |
O4—C10—C9 | 106.4 (2) | C19—C20—H20 | 119.8 |
O5—C10—C9 | 109.7 (3) | C22—C21—C20 | 120.8 (4) |
O4—C10—H10 | 110.7 | C22—C21—H21 | 119.6 |
O5—C10—H10 | 110.7 | C20—C21—H21 | 119.6 |
C9—C10—H10 | 110.7 | C21—C22—C23 | 119.1 (4) |
O5—C11—C17 | 109.9 (2) | C21—C22—H22 | 120.5 |
O5—C11—C12 | 109.1 (2) | C23—C22—H22 | 120.5 |
C17—C11—C12 | 108.2 (3) | C22—C23—C24 | 120.5 (4) |
O5—C11—H11 | 109.9 | C22—C23—H23 | 119.7 |
C17—C11—H11 | 109.9 | C24—C23—H23 | 119.7 |
C12—C11—H11 | 109.9 | C19—C24—C23 | 120.8 (4) |
O7—C12—C13 | 109.5 (2) | C19—C24—H24 | 119.6 |
O7—C12—C11 | 108.3 (2) | C23—C24—H24 | 119.6 |
C8—N1—C1—O1 | −179.4 (3) | C14—O4—C10—C9 | 176.6 (3) |
C9—N1—C1—O1 | 5.9 (5) | C11—O5—C10—O4 | −177.5 (2) |
C8—N1—C1—C2 | 0.6 (3) | C11—O5—C10—C9 | −61.6 (3) |
C9—N1—C1—C2 | −174.1 (2) | N1—C9—C10—O4 | −59.2 (3) |
O1—C1—C2—C3 | −0.2 (6) | C13—C9—C10—O4 | 171.6 (2) |
N1—C1—C2—C3 | 179.8 (3) | N1—C9—C10—O5 | −176.4 (2) |
O1—C1—C2—C7 | 178.8 (4) | C13—C9—C10—O5 | 54.4 (3) |
N1—C1—C2—C7 | −1.2 (3) | C10—O5—C11—C17 | −176.2 (3) |
C7—C2—C3—C4 | −1.6 (5) | C10—O5—C11—C12 | 65.3 (3) |
C1—C2—C3—C4 | 177.4 (3) | C18—O7—C12—C13 | 178.7 (2) |
C7—C2—C3—Cl4 | 176.9 (3) | C18—O7—C12—C11 | −59.3 (3) |
C1—C2—C3—Cl4 | −4.2 (5) | O5—C11—C12—O7 | 178.2 (2) |
C2—C3—C4—C5 | 1.8 (5) | C17—C11—C12—O7 | 58.6 (3) |
Cl4—C3—C4—C5 | −176.6 (3) | O5—C11—C12—C13 | −61.1 (3) |
C2—C3—C4—Cl3 | −178.4 (3) | C17—C11—C12—C13 | 179.3 (2) |
Cl4—C3—C4—Cl3 | 3.2 (5) | O7—C12—C13—O3 | −70.1 (3) |
C3—C4—C5—C6 | −0.2 (5) | C11—C12—C13—O3 | 169.9 (2) |
Cl3—C4—C5—C6 | 179.9 (3) | O7—C12—C13—C9 | 172.2 (2) |
C3—C4—C5—Cl2 | −179.5 (3) | C11—C12—C13—C9 | 52.2 (3) |
Cl3—C4—C5—Cl2 | 0.7 (4) | N1—C9—C13—O3 | 62.4 (3) |
C4—C5—C6—C7 | −1.6 (5) | C10—C9—C13—O3 | −170.2 (2) |
Cl2—C5—C6—C7 | 177.7 (3) | N1—C9—C13—C12 | −176.6 (2) |
C4—C5—C6—Cl1 | 178.5 (3) | C10—C9—C13—C12 | −49.3 (3) |
Cl2—C5—C6—Cl1 | −2.3 (4) | C10—O4—C14—C15 | 176.7 (3) |
C5—C6—C7—C2 | 1.8 (5) | O4—C14—C15—C16 | −7.3 (6) |
Cl1—C6—C7—C2 | −178.2 (2) | C18—O6—C17—C11 | 58.9 (3) |
C5—C6—C7—C8 | −179.1 (3) | O5—C11—C17—O6 | −176.7 (2) |
Cl1—C6—C7—C8 | 0.9 (5) | C12—C11—C17—O6 | −57.7 (3) |
C3—C2—C7—C6 | −0.3 (5) | C17—O6—C18—O7 | −60.0 (3) |
C1—C2—C7—C6 | −179.4 (3) | C17—O6—C18—C19 | 178.7 (2) |
C3—C2—C7—C8 | −179.5 (3) | C12—O7—C18—O6 | 59.9 (3) |
C1—C2—C7—C8 | 1.3 (3) | C12—O7—C18—C19 | −179.2 (2) |
C1—N1—C8—O2 | 179.8 (3) | O6—C18—C19—C24 | 108.5 (4) |
C9—N1—C8—O2 | −5.9 (5) | O7—C18—C19—C24 | −13.9 (4) |
C1—N1—C8—C7 | 0.2 (3) | O6—C18—C19—C20 | −72.4 (4) |
C9—N1—C8—C7 | 174.5 (3) | O7—C18—C19—C20 | 165.2 (3) |
C6—C7—C8—O2 | 0.3 (6) | C24—C19—C20—C21 | 0.5 (6) |
C2—C7—C8—O2 | 179.5 (3) | C18—C19—C20—C21 | −178.6 (3) |
C6—C7—C8—N1 | 179.9 (3) | C19—C20—C21—C22 | −1.0 (7) |
C2—C7—C8—N1 | −0.9 (3) | C20—C21—C22—C23 | 1.3 (7) |
C8—N1—C9—C13 | 57.2 (4) | C21—C22—C23—C24 | −1.1 (7) |
C1—N1—C9—C13 | −129.0 (3) | C20—C19—C24—C23 | −0.3 (6) |
C8—N1—C9—C10 | −71.8 (3) | C18—C19—C24—C23 | 178.8 (4) |
C1—N1—C9—C10 | 102.1 (3) | C22—C23—C24—C19 | 0.7 (7) |
C14—O4—C10—O5 | −65.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 2.10 | 2.905 (3) | 167 |
Symmetry code: (i) x+1/2, −y+1/2, −z. |