Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026043/bv2022sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026043/bv2022Isup2.hkl |
CCDC reference: 618785
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- Disorder in main residue
- R factor = 0.084
- wR factor = 0.254
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.97 Deg. PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for S1
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.835 0.970 Tmin(prime) and Tmax expected: 0.955 0.970 RR(prime) = 0.874 Please check that your absorption correction is appropriate. RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.254 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.87 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 14.00 Deg. C21A -S1 -C21 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.30 Deg. C19 -C18 -C19A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1977); cell refinement: CAD-4 Software; data reduction: SDPe (Enraf–Nonius, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXTL.
C23H16O4S | F(000) = 1616 |
Mr = 388.42 | Dx = 1.390 Mg m−3 |
Monoclinic, C2/c | Melting point: 493 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6396 (10) Å | Cell parameters from 25 reflections |
b = 15.3834 (10) Å | θ = 11.4–12.1° |
c = 22.6827 (10) Å | µ = 0.20 mm−1 |
β = 91.405 (10)° | T = 293 K |
V = 3711.4 (5) Å3 | Irregular block, colorless |
Z = 8 | 0.22 × 0.2 × 0.15 mm |
Enraf–Nonius CAD4 diffractometer | 2063 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 27.0°, θmin = 2.3° |
ω–2θ scans | h = −13→13 |
Absorption correction: ψ scan average of 2 ψ scans;(North et al., 1968) | k = 0→19 |
Tmin = 0.835, Tmax = 0.970 | l = 0→28 |
4131 measured reflections | 3 standard reflections every 200 reflections |
4035 independent reflections | intensity decay: none |
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)] = 0.084 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.254 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1153P)2 + 1.7754P] where P = (Fo2 + 2Fc2)/3 |
3247 reflections | (Δ/σ)max < 0.001 |
260 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
Experimental. The 1H NMR spectra of (I) were obtained on a Bruker DRX-250 s pectrometer at 250.13 MHz in different solvents (See text) at 20 οC. Chemical shifts (δ) are expressed in parts per million (p.p.m.) from tetramethylsilane as an internal standard. 1H NMR (250 MHz, deuteriochloroform) δ = 3.61 (3H, s, OCH3), 4.12 (1H, d, J = 1.3 Hz, H-10), 5.33 (1H, d, J = 1.3 Hz, H-9), 6.73–6.79 (2H, m, Th—H), 7.01 (1H, dd, J = 1.5, 4.8 Hz, Th—H), 7.29–7.53 (4H, m, Ph—H), 7.65–7.75 (2H, m, Ph—H), 7.99 (1H, dd, J = 1.3, 7.6 Hz, Ph—H), 8.36 (1H, dm, J = 7.6 Hz, Ph—H). 1H NMR (250 MHz, DMSOd6) δ = 3.53 (3H, s, OCH3), 4.37 (1H, d, J = 1.3 Hz, H-10), 5.46 (1H, d, J = 1.3 Hz, H-9), 6.81 (1H, dd, J = 3.5 & 5 Hz, Th—H), 7.00 (1H, d, J = 3.3 Hz, Th—H), 7.20 (1H, dd, J = 1.3 & 5 Hz, Th—H),7.38–7.52 (3H, m, Ph—H), 7.59–7.66 (1H, m, Ph—H), 7.80 (1H, d, J = 7.6 Hz, Ph—H), 7.88–7.90 (2H, m, Ph—H), 8.25 (1H, d, J = 7.8 Hz, Ph—H). |
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 | Occ. (<1) | |
C20A | −0.1369 (15) | 0.1496 (10) | 0.3203 (7) | 0.059 (5)* | 0.50 |
H20A | −0.2075 | 0.1423 | 0.2958 | 0.071* | 0.50 |
C21A | −0.0757 (15) | 0.0801 (11) | 0.3446 (7) | 0.044 (5)* | 0.50 |
H21A | −0.0994 | 0.0225 | 0.3388 | 0.053* | 0.50 |
C19 | −0.0473 (18) | 0.2262 (14) | 0.3174 (10) | 0.034 (5) | 0.50 |
H19 | −0.0590 | 0.2785 | 0.2975 | 0.041* | 0.50 |
C19A | −0.0863 (17) | 0.2384 (15) | 0.3345 (10) | 0.036 (5) | 0.50 |
H19A | −0.1193 | 0.2926 | 0.3244 | 0.043* | 0.50 |
S1 | 0.0431 (2) | 0.11058 (12) | 0.38466 (12) | 0.0919 (9) | |
O1 | 0.0381 (4) | 0.5109 (2) | 0.34852 (18) | 0.0464 (11) | |
O4 | 0.4442 (4) | 0.3489 (3) | 0.39362 (19) | 0.0671 (14) | |
O3 | 0.3262 (4) | 0.3234 (3) | 0.4689 (2) | 0.0714 (15) | |
O2 | −0.0884 (5) | 0.6131 (3) | 0.3763 (2) | 0.0843 (17) | |
C1 | −0.0513 (6) | 0.5410 (4) | 0.3860 (3) | 0.0569 (19) | |
C2 | −0.0903 (5) | 0.4826 (4) | 0.4324 (3) | 0.0466 (16) | |
C3 | −0.1804 (6) | 0.5120 (5) | 0.4717 (3) | 0.062 (2) | |
H3 | −0.2131 | 0.5678 | 0.4679 | 0.074* | |
C4 | −0.2201 (6) | 0.4587 (6) | 0.5156 (4) | 0.068 (2) | |
H4 | −0.2800 | 0.4782 | 0.5417 | 0.082* | |
C5 | −0.1711 (6) | 0.3748 (6) | 0.5215 (3) | 0.071 (2) | |
H5 | −0.1976 | 0.3386 | 0.5515 | 0.085* | |
C6 | −0.0833 (6) | 0.3465 (4) | 0.4824 (3) | 0.0552 (17) | |
H6 | −0.0516 | 0.2904 | 0.4864 | 0.066* | |
C7 | −0.0404 (5) | 0.3988 (4) | 0.4373 (3) | 0.0396 (14) | |
C8 | 0.0540 (5) | 0.3728 (3) | 0.3965 (2) | 0.0340 (13) | |
C9 | 0.1139 (5) | 0.2830 (3) | 0.3983 (2) | 0.0346 (13) | |
H9 | 0.1236 | 0.2660 | 0.4398 | 0.042* | |
C10 | 0.2458 (5) | 0.2855 (3) | 0.3721 (2) | 0.0367 (14) | |
H10 | 0.2701 | 0.2252 | 0.3642 | 0.044* | |
C11 | 0.2488 (5) | 0.3333 (4) | 0.3149 (2) | 0.0386 (14) | |
C12 | 0.3297 (6) | 0.3094 (5) | 0.2710 (3) | 0.0537 (18) | |
H12 | 0.3789 | 0.2598 | 0.2754 | 0.064* | |
C13 | 0.3376 (7) | 0.3589 (6) | 0.2209 (3) | 0.073 (2) | |
H13 | 0.3923 | 0.3424 | 0.1916 | 0.088* | |
C14 | 0.2662 (7) | 0.4323 (6) | 0.2135 (3) | 0.071 (2) | |
H14 | 0.2728 | 0.4653 | 0.1793 | 0.085* | |
C15 | 0.1856 (6) | 0.4571 (4) | 0.2560 (3) | 0.0482 (16) | |
H15 | 0.1374 | 0.5071 | 0.2508 | 0.058* | |
C16 | 0.1747 (5) | 0.4076 (4) | 0.3076 (3) | 0.0397 (14) | |
C17 | 0.0884 (5) | 0.4273 (3) | 0.3540 (3) | 0.0368 (14) | |
C18 | 0.0282 (5) | 0.2176 (3) | 0.3683 (3) | 0.0412 (15) | |
C20 | −0.1045 (14) | 0.1467 (10) | 0.2991 (7) | 0.052 (4)* | 0.50 |
H20 | −0.1662 | 0.1428 | 0.2694 | 0.062* | 0.50 |
C21 | −0.0639 (18) | 0.0848 (14) | 0.3263 (8) | 0.062 (6)* | 0.50 |
H21 | −0.0872 | 0.0280 | 0.3173 | 0.075* | 0.50 |
C22 | 0.3408 (5) | 0.3218 (4) | 0.4174 (3) | 0.0403 (15) | |
C23 | 0.5443 (6) | 0.3790 (5) | 0.4335 (3) | 0.072 (2) | |
H23A | 0.6150 | 0.3972 | 0.4110 | 0.108* | |
H23B | 0.5694 | 0.3327 | 0.4595 | 0.108* | |
H23C | 0.5146 | 0.4272 | 0.4562 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C19 | 0.037 (13) | 0.018 (8) | 0.048 (12) | 0.001 (8) | −0.004 (8) | −0.019 (7) |
C19A | 0.018 (10) | 0.022 (8) | 0.066 (15) | 0.004 (7) | −0.007 (8) | −0.026 (8) |
S1 | 0.1002 (17) | 0.0469 (12) | 0.126 (2) | −0.0122 (11) | −0.0441 (15) | 0.0090 (12) |
O1 | 0.052 (3) | 0.029 (2) | 0.057 (3) | 0.0101 (19) | −0.009 (2) | −0.001 (2) |
O4 | 0.048 (3) | 0.105 (4) | 0.048 (3) | −0.034 (3) | −0.005 (2) | 0.004 (3) |
O3 | 0.055 (3) | 0.112 (4) | 0.047 (3) | −0.020 (3) | −0.007 (2) | −0.003 (3) |
O2 | 0.093 (4) | 0.050 (3) | 0.110 (4) | 0.042 (3) | −0.006 (3) | 0.002 (3) |
C1 | 0.057 (4) | 0.046 (4) | 0.067 (5) | 0.022 (3) | −0.017 (4) | −0.015 (4) |
C2 | 0.033 (3) | 0.054 (4) | 0.052 (4) | 0.011 (3) | −0.013 (3) | −0.015 (3) |
C3 | 0.041 (4) | 0.075 (5) | 0.069 (5) | 0.012 (4) | −0.011 (4) | −0.028 (4) |
C4 | 0.028 (4) | 0.107 (7) | 0.071 (6) | 0.008 (4) | 0.000 (4) | −0.039 (5) |
C5 | 0.048 (4) | 0.104 (7) | 0.061 (5) | −0.015 (4) | 0.009 (4) | −0.010 (5) |
C6 | 0.055 (4) | 0.054 (4) | 0.057 (4) | −0.006 (3) | 0.007 (4) | 0.000 (4) |
C7 | 0.030 (3) | 0.042 (3) | 0.046 (4) | 0.002 (3) | −0.007 (3) | −0.009 (3) |
C8 | 0.036 (3) | 0.025 (3) | 0.040 (3) | 0.004 (2) | −0.006 (3) | −0.002 (3) |
C9 | 0.038 (3) | 0.028 (3) | 0.037 (3) | 0.003 (2) | −0.007 (3) | 0.005 (2) |
C10 | 0.032 (3) | 0.029 (3) | 0.049 (4) | 0.003 (2) | −0.001 (3) | −0.001 (3) |
C11 | 0.030 (3) | 0.048 (4) | 0.037 (3) | −0.004 (3) | −0.003 (3) | −0.003 (3) |
C12 | 0.040 (4) | 0.071 (5) | 0.050 (4) | 0.008 (3) | −0.004 (3) | −0.005 (4) |
C13 | 0.047 (4) | 0.125 (7) | 0.048 (5) | 0.014 (5) | 0.005 (3) | 0.004 (5) |
C14 | 0.054 (5) | 0.114 (7) | 0.045 (5) | 0.000 (5) | −0.002 (4) | 0.013 (5) |
C15 | 0.048 (4) | 0.051 (4) | 0.045 (4) | −0.003 (3) | −0.015 (3) | 0.009 (3) |
C16 | 0.039 (3) | 0.042 (3) | 0.038 (3) | −0.004 (3) | −0.008 (3) | 0.002 (3) |
C17 | 0.031 (3) | 0.029 (3) | 0.050 (4) | 0.010 (2) | −0.012 (3) | −0.004 (3) |
C18 | 0.040 (3) | 0.028 (3) | 0.055 (4) | −0.005 (3) | −0.002 (3) | 0.003 (3) |
C22 | 0.038 (3) | 0.041 (4) | 0.042 (4) | 0.006 (3) | −0.008 (3) | 0.006 (3) |
C23 | 0.054 (4) | 0.097 (6) | 0.065 (5) | −0.033 (4) | −0.018 (4) | 0.011 (4) |
C20A—C21A | 1.36 (2) | C6—H6 | 0.9300 |
C20A—C19A | 1.50 (3) | C7—C8 | 1.438 (8) |
C20A—H20A | 0.9300 | C8—C17 | 1.336 (7) |
C21A—S1 | 1.607 (16) | C8—C9 | 1.521 (7) |
C21A—H21A | 0.9300 | C9—C18 | 1.510 (7) |
C19—C18 | 1.40 (2) | C9—C10 | 1.538 (7) |
C19—C20 | 1.42 (3) | C9—H9 | 0.9800 |
C19—H19 | 0.9300 | C10—C11 | 1.492 (8) |
C19A—C18 | 1.46 (2) | C10—C22 | 1.530 (8) |
C19A—H19A | 0.9300 | C10—H10 | 0.9800 |
S1—C18 | 1.694 (6) | C11—C12 | 1.382 (8) |
S1—C21 | 1.770 (19) | C11—C16 | 1.397 (8) |
O1—C1 | 1.372 (8) | C12—C13 | 1.372 (9) |
O1—C17 | 1.398 (6) | C12—H12 | 0.9300 |
O4—C22 | 1.306 (7) | C13—C14 | 1.368 (10) |
O4—C23 | 1.456 (7) | C13—H13 | 0.9300 |
O3—C22 | 1.181 (7) | C14—C15 | 1.361 (9) |
O2—C1 | 1.195 (7) | C14—H14 | 0.9300 |
C1—C2 | 1.453 (9) | C15—C16 | 1.404 (8) |
C2—C7 | 1.398 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.400 (9) | C16—C17 | 1.446 (8) |
C3—C4 | 1.366 (10) | C20—C21 | 1.21 (2) |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.396 (10) | C21—H21 | 0.9300 |
C4—H4 | 0.9300 | C23—H23A | 0.9600 |
C5—C6 | 1.373 (9) | C23—H23B | 0.9600 |
C5—H5 | 0.9300 | C23—H23C | 0.9600 |
C6—C7 | 1.388 (8) | ||
C21A—C20A—C19A | 117.5 (16) | C11—C10—C9 | 112.8 (4) |
C21A—C20A—H20A | 121.2 | C22—C10—C9 | 110.0 (5) |
C19A—C20A—H20A | 121.2 | C11—C10—H10 | 107.2 |
C20A—C21A—S1 | 111.2 (13) | C22—C10—H10 | 107.2 |
C20A—C21A—H21A | 124.4 | C9—C10—H10 | 107.2 |
S1—C21A—H21A | 124.4 | C12—C11—C16 | 119.4 (6) |
C18—C19—C20 | 113.2 (18) | C12—C11—C10 | 121.6 (5) |
C18—C19—H19 | 123.4 | C16—C11—C10 | 118.8 (5) |
C20—C19—H19 | 123.4 | C13—C12—C11 | 120.1 (7) |
C18—C19A—C20A | 101.7 (15) | C13—C12—H12 | 119.9 |
C18—C19A—H19A | 129.1 | C11—C12—H12 | 119.9 |
C20A—C19A—H19A | 129.1 | C14—C13—C12 | 121.0 (7) |
C21A—S1—C18 | 95.3 (6) | C14—C13—H13 | 119.5 |
C21A—S1—C21 | 14.0 (9) | C12—C13—H13 | 119.5 |
C18—S1—C21 | 89.9 (7) | C15—C14—C13 | 120.1 (7) |
C1—O1—C17 | 121.7 (5) | C15—C14—H14 | 120.0 |
C22—O4—C23 | 117.1 (5) | C13—C14—H14 | 120.0 |
O2—C1—O1 | 115.5 (7) | C14—C15—C16 | 120.3 (6) |
O2—C1—C2 | 127.5 (7) | C14—C15—H15 | 119.8 |
O1—C1—C2 | 117.1 (5) | C16—C15—H15 | 119.8 |
C7—C2—C3 | 120.8 (7) | C11—C16—C15 | 119.1 (6) |
C7—C2—C1 | 120.9 (6) | C11—C16—C17 | 116.9 (5) |
C3—C2—C1 | 118.3 (6) | C15—C16—C17 | 124.0 (5) |
C4—C3—C2 | 120.0 (7) | C8—C17—O1 | 122.1 (5) |
C4—C3—H3 | 120.0 | C8—C17—C16 | 125.8 (5) |
C2—C3—H3 | 120.0 | O1—C17—C16 | 112.1 (5) |
C3—C4—C5 | 120.2 (7) | C19—C18—C19A | 24.3 (8) |
C3—C4—H4 | 119.9 | C19—C18—C9 | 129.7 (11) |
C5—C4—H4 | 119.9 | C19A—C18—C9 | 125.3 (10) |
C6—C5—C4 | 119.4 (8) | C19—C18—S1 | 108.8 (10) |
C6—C5—H5 | 120.3 | C19A—C18—S1 | 113.6 (10) |
C4—C5—H5 | 120.3 | C9—C18—S1 | 119.8 (4) |
C5—C6—C7 | 122.2 (7) | C21—C20—C19 | 112.5 (17) |
C5—C6—H6 | 118.9 | C21—C20—H20 | 123.8 |
C7—C6—H6 | 118.9 | C19—C20—H20 | 123.8 |
C6—C7—C2 | 117.4 (6) | C20—C21—S1 | 114.9 (16) |
C6—C7—C8 | 124.2 (5) | C20—C21—H21 | 122.5 |
C2—C7—C8 | 118.4 (6) | S1—C21—H21 | 122.5 |
C17—C8—C7 | 119.9 (5) | O3—C22—O4 | 122.3 (6) |
C17—C8—C9 | 117.9 (5) | O3—C22—C10 | 124.8 (6) |
C7—C8—C9 | 122.2 (5) | O4—C22—C10 | 112.8 (5) |
C18—C9—C8 | 110.2 (4) | O4—C23—H23A | 109.5 |
C18—C9—C10 | 112.8 (5) | O4—C23—H23B | 109.5 |
C8—C9—C10 | 110.7 (4) | H23A—C23—H23B | 109.5 |
C18—C9—H9 | 107.6 | O4—C23—H23C | 109.5 |
C8—C9—H9 | 107.6 | H23A—C23—H23C | 109.5 |
C10—C9—H9 | 107.6 | H23B—C23—H23C | 109.5 |
C11—C10—C22 | 112.1 (5) | ||
C19A—C20A—C21A—S1 | 0 (2) | C10—C11—C16—C15 | 174.4 (5) |
C21A—C20A—C19A—C18 | 5 (2) | C12—C11—C16—C17 | 177.6 (5) |
C20A—C21A—S1—C18 | −4.1 (14) | C10—C11—C16—C17 | −7.1 (7) |
C20A—C21A—S1—C21 | −72 (5) | C14—C15—C16—C11 | 0.7 (9) |
C17—O1—C1—O2 | −178.9 (5) | C14—C15—C16—C17 | −177.7 (6) |
C17—O1—C1—C2 | 1.0 (8) | C7—C8—C17—O1 | 1.9 (8) |
O2—C1—C2—C7 | 178.3 (6) | C9—C8—C17—O1 | 179.6 (4) |
O1—C1—C2—C7 | −1.5 (8) | C7—C8—C17—C16 | −175.2 (5) |
O2—C1—C2—C3 | −0.9 (10) | C9—C8—C17—C16 | 2.5 (8) |
O1—C1—C2—C3 | 179.2 (5) | C1—O1—C17—C8 | −1.2 (8) |
C7—C2—C3—C4 | 0.2 (9) | C1—O1—C17—C16 | 176.2 (5) |
C1—C2—C3—C4 | 179.4 (6) | C11—C16—C17—C8 | −14.8 (8) |
C2—C3—C4—C5 | 0.1 (10) | C15—C16—C17—C8 | 163.6 (6) |
C3—C4—C5—C6 | −0.5 (10) | C11—C16—C17—O1 | 167.8 (5) |
C4—C5—C6—C7 | 0.6 (10) | C15—C16—C17—O1 | −13.7 (7) |
C5—C6—C7—C2 | −0.3 (9) | C20—C19—C18—C19A | −97 (5) |
C5—C6—C7—C8 | 178.1 (6) | C20—C19—C18—C9 | 173.5 (10) |
C3—C2—C7—C6 | −0.1 (8) | C20—C19—C18—S1 | 8.7 (15) |
C1—C2—C7—C6 | −179.3 (5) | C20A—C19A—C18—C19 | 75 (4) |
C3—C2—C7—C8 | −178.6 (5) | C20A—C19A—C18—C9 | −175.2 (9) |
C1—C2—C7—C8 | 2.2 (8) | C20A—C19A—C18—S1 | −8.1 (14) |
C6—C7—C8—C17 | 179.2 (5) | C8—C9—C18—C19 | 39.0 (11) |
C2—C7—C8—C17 | −2.4 (8) | C10—C9—C18—C19 | −85.3 (10) |
C6—C7—C8—C9 | 1.7 (8) | C8—C9—C18—C19A | 8.7 (12) |
C2—C7—C8—C9 | 180.0 (5) | C10—C9—C18—C19A | −115.6 (11) |
C17—C8—C9—C18 | −97.2 (6) | C8—C9—C18—S1 | −157.7 (4) |
C7—C8—C9—C18 | 80.4 (6) | C10—C9—C18—S1 | 78.0 (6) |
C17—C8—C9—C10 | 28.3 (7) | C21A—S1—C18—C19 | −17.9 (10) |
C7—C8—C9—C10 | −154.1 (5) | C21—S1—C18—C19 | −4.9 (10) |
C18—C9—C10—C11 | 77.2 (6) | C21A—S1—C18—C19A | 7.7 (11) |
C8—C9—C10—C11 | −46.8 (6) | C21—S1—C18—C19A | 20.7 (10) |
C18—C9—C10—C22 | −156.8 (5) | C21A—S1—C18—C9 | 175.6 (7) |
C8—C9—C10—C22 | 79.2 (5) | C21—S1—C18—C9 | −171.4 (8) |
C22—C10—C11—C12 | 87.9 (6) | C18—C19—C20—C21 | −9 (2) |
C9—C10—C11—C12 | −147.2 (5) | C19—C20—C21—S1 | 5 (2) |
C22—C10—C11—C16 | −87.3 (6) | C21A—S1—C21—C20 | 112 (5) |
C9—C10—C11—C16 | 37.7 (7) | C18—S1—C21—C20 | −0.2 (16) |
C16—C11—C12—C13 | 0.5 (9) | C23—O4—C22—O3 | 2.0 (10) |
C10—C11—C12—C13 | −174.7 (6) | C23—O4—C22—C10 | −175.8 (5) |
C11—C12—C13—C14 | 0.0 (11) | C11—C10—C22—O3 | 147.2 (6) |
C12—C13—C14—C15 | −0.2 (11) | C9—C10—C22—O3 | 20.8 (8) |
C13—C14—C15—C16 | −0.2 (10) | C11—C10—C22—O4 | −35.0 (7) |
C12—C11—C16—C15 | −0.9 (8) | C9—C10—C22—O4 | −161.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O2i | 0.98 | 2.30 | 3.185 (8) | 150 |
C9—H9···O3ii | 0.98 | 2.53 | 3.473 (7) | 161 |
C3—H3···O3iii | 0.93 | 2.53 | 3.277 (9) | 138 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, −y+1/2, −z+1; (iii) −x, −y+1, −z+1. |
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