The title compound, C27H24Cl3N3O7S, contains a thiadiazoline ring which is almost planar. The two ethoxy groups bonded at the 3a- and 4-positions are in a trans configuration.
Supporting information
CCDC reference: 264067
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.115
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.525 0.885
Tmin' and Tmax expected: 0.797 0.885
RR' = 0.658
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.66
PLAT430_ALERT_2_B Short Inter D...A Contact O6 .. O6 .. 2.81 Ang.
Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.37 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C24 - C25 ... 1.40 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3 .. O7 .. 3.15 Ang.
PLAT725_ALERT_1_C D-H Calc 0.96000, Rep 0.98000 Dev... 0.02 Ang.
C25 -H25C 1.555 1.555
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.
(±)-(3aRS,4SR)-9-Chloro-3a,4-diethoxy-6,8-dimethoxy-2-
(2-chloro-4-nitrophenyl)-4-(4-chlorophenyl)chromano[4,3-
d]-Δ
1,9 b-1,2,3- thiadiazoline
top
Crystal data top
C27H24Cl3N3O7S | F(000) = 1320 |
Mr = 640.90 | Dx = 1.460 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3365 reflections |
a = 18.285 (4) Å | θ = 4.7–46.5° |
b = 10.779 (3) Å | µ = 0.44 mm−1 |
c = 16.152 (4) Å | T = 293 K |
β = 113.652 (4)° | Prism, yellow |
V = 2916.0 (12) Å3 | 0.51 × 0.34 × 0.28 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6336 independent reflections |
Radiation source: fine-focus sealed tube | 3679 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
φ and ω scans | θmax = 27.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→23 |
Tmin = 0.525, Tmax = 0.885 | k = −13→11 |
16701 measured reflections | l = −20→20 |
Refinement top
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) = 0.115 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0469P)2] where P = (Fo2 + 2Fc2)/3 |
6336 reflections | (Δ/σ)max = 0.016 |
374 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.26781 (4) | 0.03540 (6) | 0.27000 (4) | 0.04978 (19) | |
Cl1 | 0.12097 (5) | 0.61934 (7) | 0.28349 (5) | 0.0866 (3) | |
Cl2 | −0.06839 (5) | 0.11879 (8) | −0.12656 (5) | 0.0948 (3) | |
Cl3 | 0.39330 (6) | −0.16700 (8) | 0.28287 (5) | 0.0891 (3) | |
O1 | 0.16601 (9) | 0.37258 (14) | 0.25807 (11) | 0.0514 (4) | |
O2 | 0.15190 (9) | 0.13948 (14) | 0.31185 (10) | 0.0466 (4) | |
O3 | 0.26481 (10) | 0.30205 (15) | 0.21388 (11) | 0.0541 (5) | |
O4 | 0.36596 (10) | 0.31688 (15) | 0.55440 (11) | 0.0546 (5) | |
O5 | 0.21016 (11) | 0.69198 (17) | 0.46540 (13) | 0.0731 (6) | |
O6 | 0.53535 (13) | −0.42227 (19) | 0.57534 (14) | 0.0814 (7) | |
O7 | 0.50645 (15) | −0.3398 (2) | 0.67827 (15) | 0.0935 (7) | |
N1 | 0.35440 (11) | 0.05384 (18) | 0.37102 (14) | 0.0500 (5) | |
N2 | 0.35202 (11) | 0.16048 (18) | 0.41714 (14) | 0.0493 (5) | |
N3 | 0.50542 (13) | −0.3413 (2) | 0.60280 (16) | 0.0578 (6) | |
C1 | 0.28706 (13) | 0.2219 (2) | 0.37928 (15) | 0.0403 (6) | |
C2 | 0.22047 (13) | 0.1678 (2) | 0.29671 (15) | 0.0405 (6) | |
C3 | 0.19490 (14) | 0.2696 (2) | 0.22357 (15) | 0.0451 (6) | |
C4 | 0.21093 (13) | 0.4139 (2) | 0.34329 (15) | 0.0441 (6) | |
C5 | 0.27077 (13) | 0.3426 (2) | 0.40713 (16) | 0.0421 (6) | |
C6 | 0.31102 (13) | 0.3920 (2) | 0.49422 (16) | 0.0447 (6) | |
C7 | 0.29211 (14) | 0.5086 (2) | 0.51549 (17) | 0.0515 (7) | |
H7 | 0.3192 | 0.5406 | 0.5733 | 0.062* | |
C8 | 0.23291 (15) | 0.5776 (2) | 0.45068 (18) | 0.0533 (7) | |
C9 | 0.19252 (14) | 0.5308 (2) | 0.36403 (17) | 0.0516 (7) | |
C10 | 0.12749 (14) | 0.2320 (2) | 0.13610 (15) | 0.0444 (6) | |
C11 | 0.04865 (14) | 0.2425 (2) | 0.12398 (17) | 0.0551 (7) | |
H11 | 0.0359 | 0.2739 | 0.1702 | 0.066* | |
C12 | −0.01145 (16) | 0.2063 (3) | 0.04331 (19) | 0.0631 (8) | |
H12 | −0.0646 | 0.2133 | 0.0351 | 0.076* | |
C13 | 0.00754 (19) | 0.1603 (3) | −0.02407 (18) | 0.0620 (8) | |
C14 | 0.0853 (2) | 0.1455 (3) | −0.01268 (18) | 0.0690 (8) | |
H14 | 0.0976 | 0.1112 | −0.0583 | 0.083* | |
C15 | 0.14507 (17) | 0.1824 (2) | 0.06779 (17) | 0.0578 (7) | |
H15 | 0.1981 | 0.1737 | 0.0760 | 0.069* | |
C16 | 0.38885 (13) | −0.0472 (2) | 0.42789 (16) | 0.0432 (6) | |
C17 | 0.40957 (14) | −0.1551 (2) | 0.39528 (16) | 0.0491 (6) | |
C18 | 0.44683 (14) | −0.2518 (2) | 0.45190 (16) | 0.0505 (6) | |
H18 | 0.4595 | −0.3242 | 0.4292 | 0.061* | |
C19 | 0.46481 (13) | −0.2397 (2) | 0.54181 (16) | 0.0454 (6) | |
C20 | 0.44791 (15) | −0.1336 (2) | 0.57749 (17) | 0.0529 (7) | |
H20 | 0.4623 | −0.1264 | 0.6394 | 0.063* | |
C21 | 0.40933 (14) | −0.0381 (2) | 0.52017 (17) | 0.0505 (6) | |
H21 | 0.3968 | 0.0336 | 0.5436 | 0.061* | |
C22 | 0.40566 (16) | 0.3579 (3) | 0.64496 (16) | 0.0608 (7) | |
H22A | 0.4351 | 0.4321 | 0.6463 | 0.091* | |
H22B | 0.4417 | 0.2945 | 0.6800 | 0.091* | |
H22C | 0.3670 | 0.3748 | 0.6699 | 0.091* | |
C23 | 0.24407 (17) | 0.7393 (3) | 0.5543 (2) | 0.0883 (11) | |
H23A | 0.2333 | 0.6834 | 0.5943 | 0.133* | |
H23B | 0.2213 | 0.8190 | 0.5560 | 0.133* | |
H23C | 0.3007 | 0.7476 | 0.5731 | 0.133* | |
C24 | 0.26154 (19) | 0.4102 (3) | 0.1601 (2) | 0.0812 (10) | |
H24A | 0.2708 | 0.3854 | 0.1074 | 0.097* | |
H24B | 0.2085 | 0.4462 | 0.1392 | 0.097* | |
C25 | 0.3178 (2) | 0.4998 (4) | 0.2079 (3) | 0.1358 (19) | |
H25A | 0.3007 | 0.5408 | 0.2499 | 0.140* | |
H25B | 0.3228 | 0.5595 | 0.1664 | 0.140* | |
H25C | 0.3685 | 0.4606 | 0.2404 | 0.140* | |
C26 | 0.16298 (17) | 0.0571 (3) | 0.38471 (19) | 0.0699 (9) | |
H26A | 0.1967 | 0.0958 | 0.4415 | 0.084* | |
H26B | 0.1890 | −0.0182 | 0.3778 | 0.084* | |
C27 | 0.08415 (19) | 0.0271 (3) | 0.3850 (2) | 0.0957 (12) | |
H27A | 0.0563 | 0.1025 | 0.3852 | 0.140* | |
H27B | 0.0914 | −0.0205 | 0.4380 | 0.140* | |
H27C | 0.0536 | −0.0203 | 0.3321 | 0.140* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0527 (4) | 0.0429 (4) | 0.0433 (4) | 0.0101 (3) | 0.0085 (3) | −0.0003 (3) |
Cl1 | 0.0875 (6) | 0.0580 (5) | 0.0733 (5) | 0.0326 (4) | −0.0106 (4) | −0.0036 (4) |
Cl2 | 0.1051 (7) | 0.0809 (6) | 0.0543 (5) | −0.0064 (5) | −0.0140 (4) | −0.0046 (4) |
Cl3 | 0.1297 (7) | 0.0817 (6) | 0.0510 (4) | 0.0537 (5) | 0.0312 (4) | 0.0102 (4) |
O1 | 0.0516 (10) | 0.0390 (10) | 0.0466 (10) | 0.0102 (7) | 0.0017 (8) | −0.0014 (8) |
O2 | 0.0396 (10) | 0.0481 (10) | 0.0470 (10) | −0.0008 (7) | 0.0122 (8) | 0.0059 (8) |
O3 | 0.0471 (10) | 0.0541 (11) | 0.0543 (11) | 0.0006 (8) | 0.0131 (8) | 0.0200 (9) |
O4 | 0.0585 (11) | 0.0455 (10) | 0.0418 (10) | 0.0082 (8) | 0.0015 (8) | 0.0020 (8) |
O5 | 0.0735 (13) | 0.0471 (12) | 0.0742 (13) | 0.0156 (9) | 0.0041 (10) | −0.0180 (10) |
O6 | 0.1100 (17) | 0.0485 (12) | 0.0686 (14) | 0.0257 (11) | 0.0181 (12) | 0.0048 (11) |
O7 | 0.137 (2) | 0.0879 (17) | 0.0559 (14) | 0.0337 (14) | 0.0392 (14) | 0.0240 (12) |
N1 | 0.0437 (12) | 0.0375 (12) | 0.0540 (13) | 0.0059 (9) | 0.0040 (10) | −0.0013 (10) |
N2 | 0.0414 (12) | 0.0365 (12) | 0.0560 (13) | 0.0013 (9) | 0.0048 (10) | −0.0029 (10) |
N3 | 0.0628 (15) | 0.0447 (14) | 0.0531 (15) | 0.0030 (11) | 0.0098 (12) | 0.0056 (12) |
C1 | 0.0372 (13) | 0.0351 (13) | 0.0419 (13) | 0.0004 (10) | 0.0089 (11) | 0.0054 (11) |
C2 | 0.0390 (14) | 0.0374 (13) | 0.0404 (13) | 0.0010 (10) | 0.0109 (11) | −0.0004 (11) |
C3 | 0.0456 (15) | 0.0398 (14) | 0.0435 (14) | 0.0054 (11) | 0.0112 (12) | 0.0033 (11) |
C4 | 0.0443 (14) | 0.0366 (14) | 0.0431 (14) | −0.0014 (11) | 0.0087 (11) | −0.0014 (11) |
C5 | 0.0419 (14) | 0.0333 (13) | 0.0443 (14) | 0.0011 (10) | 0.0101 (11) | 0.0029 (11) |
C6 | 0.0413 (14) | 0.0404 (15) | 0.0448 (14) | 0.0004 (11) | 0.0093 (11) | 0.0046 (12) |
C7 | 0.0492 (15) | 0.0446 (15) | 0.0497 (15) | −0.0032 (12) | 0.0082 (12) | −0.0076 (13) |
C8 | 0.0521 (16) | 0.0355 (14) | 0.0622 (17) | 0.0009 (11) | 0.0123 (13) | −0.0052 (13) |
C9 | 0.0479 (15) | 0.0390 (15) | 0.0545 (16) | 0.0077 (11) | 0.0064 (12) | −0.0013 (13) |
C10 | 0.0462 (15) | 0.0398 (14) | 0.0392 (13) | 0.0063 (11) | 0.0086 (11) | 0.0044 (11) |
C11 | 0.0464 (16) | 0.0563 (17) | 0.0512 (16) | 0.0113 (12) | 0.0077 (13) | −0.0032 (13) |
C12 | 0.0469 (16) | 0.0662 (19) | 0.0617 (18) | 0.0073 (13) | 0.0067 (14) | −0.0017 (15) |
C13 | 0.073 (2) | 0.0491 (17) | 0.0431 (16) | 0.0036 (14) | 0.0013 (14) | 0.0015 (13) |
C14 | 0.087 (2) | 0.069 (2) | 0.0472 (17) | 0.0142 (17) | 0.0223 (16) | −0.0052 (15) |
C15 | 0.0573 (17) | 0.0635 (18) | 0.0472 (16) | 0.0084 (13) | 0.0153 (13) | −0.0018 (14) |
C16 | 0.0355 (13) | 0.0384 (14) | 0.0484 (15) | 0.0026 (10) | 0.0095 (11) | 0.0025 (12) |
C17 | 0.0523 (16) | 0.0461 (15) | 0.0424 (14) | 0.0075 (12) | 0.0121 (12) | −0.0002 (12) |
C18 | 0.0535 (16) | 0.0389 (14) | 0.0527 (16) | 0.0061 (11) | 0.0145 (13) | −0.0012 (12) |
C19 | 0.0416 (14) | 0.0407 (14) | 0.0457 (15) | 0.0021 (11) | 0.0089 (11) | 0.0047 (12) |
C20 | 0.0553 (16) | 0.0529 (17) | 0.0442 (15) | 0.0028 (13) | 0.0133 (12) | −0.0001 (13) |
C21 | 0.0506 (16) | 0.0424 (15) | 0.0519 (16) | 0.0060 (12) | 0.0138 (12) | −0.0050 (13) |
C22 | 0.0605 (17) | 0.0616 (18) | 0.0443 (15) | 0.0010 (13) | 0.0043 (13) | 0.0001 (13) |
C23 | 0.068 (2) | 0.068 (2) | 0.097 (2) | 0.0096 (16) | 0.0000 (17) | −0.0429 (19) |
C24 | 0.077 (2) | 0.078 (2) | 0.069 (2) | −0.0065 (17) | 0.0097 (16) | 0.0369 (18) |
C25 | 0.113 (3) | 0.103 (3) | 0.139 (4) | −0.034 (2) | −0.004 (3) | 0.074 (3) |
C26 | 0.0621 (19) | 0.086 (2) | 0.0569 (18) | −0.0058 (16) | 0.0189 (14) | 0.0215 (16) |
C27 | 0.075 (2) | 0.105 (3) | 0.104 (3) | −0.0233 (19) | 0.032 (2) | 0.028 (2) |
Geometric parameters (Å, º) top
S1—N1 | 1.771 (2) | C11—H11 | 0.9300 |
S1—C2 | 1.809 (2) | C12—C13 | 1.362 (4) |
Cl1—C9 | 1.717 (2) | C12—H12 | 0.9300 |
Cl2—C13 | 1.739 (3) | C13—C14 | 1.367 (4) |
Cl3—C17 | 1.723 (3) | C14—C15 | 1.380 (3) |
O1—C4 | 1.364 (3) | C14—H14 | 0.9300 |
O1—C3 | 1.435 (3) | C15—H15 | 0.9300 |
O2—C2 | 1.404 (3) | C16—C21 | 1.387 (3) |
O2—C26 | 1.422 (3) | C16—C17 | 1.391 (3) |
O3—C3 | 1.393 (3) | C17—C18 | 1.373 (3) |
O3—C24 | 1.441 (3) | C18—C19 | 1.361 (3) |
O4—C6 | 1.351 (3) | C18—H18 | 0.9300 |
O4—C22 | 1.418 (3) | C19—C20 | 1.370 (3) |
O5—C8 | 1.353 (3) | C20—C21 | 1.375 (3) |
O5—C23 | 1.411 (3) | C20—H20 | 0.9300 |
O6—N3 | 1.206 (3) | C21—H21 | 0.9300 |
O7—N3 | 1.212 (3) | C22—H22A | 0.9600 |
N1—N2 | 1.380 (3) | C22—H22B | 0.9600 |
N1—C16 | 1.401 (3) | C22—H22C | 0.9600 |
N2—C1 | 1.281 (3) | C23—H23A | 0.9600 |
N3—C19 | 1.460 (3) | C23—H23B | 0.9600 |
C1—C5 | 1.447 (3) | C23—H23C | 0.9600 |
C1—C2 | 1.516 (3) | C24—C25 | 1.396 (4) |
C2—C3 | 1.541 (3) | C24—H24A | 0.9700 |
C3—C10 | 1.511 (3) | C24—H24B | 0.9700 |
C4—C9 | 1.380 (3) | C25—H25A | 0.9600 |
C4—C5 | 1.394 (3) | C25—H25B | 0.9600 |
C5—C6 | 1.405 (3) | C25—H25C | 0.9600 |
C6—C7 | 1.384 (3) | C26—C27 | 1.479 (4) |
C7—C8 | 1.382 (3) | C26—H26A | 0.9700 |
C7—H7 | 0.9300 | C26—H26B | 0.9700 |
C8—C9 | 1.389 (3) | C27—H27A | 0.9600 |
C10—C15 | 1.375 (3) | C27—H27B | 0.9600 |
C10—C11 | 1.379 (3) | C27—H27C | 0.9600 |
C11—C12 | 1.382 (3) | | |
| | | |
N1—S1—C2 | 91.62 (10) | C13—C14—H14 | 120.6 |
C4—O1—C3 | 118.55 (17) | C15—C14—H14 | 120.6 |
C2—O2—C26 | 116.05 (17) | C10—C15—C14 | 121.1 (3) |
C3—O3—C24 | 116.94 (19) | C10—C15—H15 | 119.5 |
C6—O4—C22 | 118.74 (19) | C14—C15—H15 | 119.5 |
C8—O5—C23 | 117.9 (2) | C21—C16—C17 | 117.9 (2) |
N2—N1—C16 | 113.38 (19) | C21—C16—N1 | 120.4 (2) |
N2—N1—S1 | 112.38 (14) | C17—C16—N1 | 121.4 (2) |
C16—N1—S1 | 121.17 (16) | C18—C17—C16 | 121.3 (2) |
C1—N2—N1 | 113.37 (19) | C18—C17—Cl3 | 118.4 (2) |
O6—N3—O7 | 123.6 (2) | C16—C17—Cl3 | 120.20 (19) |
O6—N3—C19 | 118.5 (2) | C19—C18—C17 | 118.8 (2) |
O7—N3—C19 | 117.9 (2) | C19—C18—H18 | 120.6 |
N2—C1—C5 | 125.7 (2) | C17—C18—H18 | 120.6 |
N2—C1—C2 | 119.0 (2) | C18—C19—C20 | 122.0 (2) |
C5—C1—C2 | 115.26 (19) | C18—C19—N3 | 119.2 (2) |
O2—C2—C1 | 112.86 (19) | C20—C19—N3 | 118.8 (2) |
O2—C2—C3 | 105.71 (17) | C19—C20—C21 | 118.9 (2) |
C1—C2—C3 | 106.88 (18) | C19—C20—H20 | 120.6 |
O2—C2—S1 | 114.61 (15) | C21—C20—H20 | 120.6 |
C1—C2—S1 | 102.76 (15) | C20—C21—C16 | 121.0 (2) |
C3—C2—S1 | 113.94 (17) | C20—C21—H21 | 119.5 |
O3—C3—O1 | 110.26 (19) | C16—C21—H21 | 119.5 |
O3—C3—C10 | 113.8 (2) | O4—C22—H22A | 109.5 |
O1—C3—C10 | 106.34 (18) | O4—C22—H22B | 109.5 |
O3—C3—C2 | 104.78 (18) | H22A—C22—H22B | 109.5 |
O1—C3—C2 | 107.39 (19) | O4—C22—H22C | 109.5 |
C10—C3—C2 | 114.14 (19) | H22A—C22—H22C | 109.5 |
O1—C4—C9 | 115.8 (2) | H22B—C22—H22C | 109.5 |
O1—C4—C5 | 122.9 (2) | O5—C23—H23A | 109.5 |
C9—C4—C5 | 121.2 (2) | O5—C23—H23B | 109.5 |
C4—C5—C6 | 118.2 (2) | H23A—C23—H23B | 109.5 |
C4—C5—C1 | 117.6 (2) | O5—C23—H23C | 109.5 |
C6—C5—C1 | 124.2 (2) | H23A—C23—H23C | 109.5 |
O4—C6—C7 | 123.6 (2) | H23B—C23—H23C | 109.5 |
O4—C6—C5 | 115.7 (2) | C25—C24—O3 | 112.5 (3) |
C7—C6—C5 | 120.7 (2) | C25—C24—H24A | 109.1 |
C8—C7—C6 | 119.9 (2) | O3—C24—H24A | 109.1 |
C8—C7—H7 | 120.1 | C25—C24—H24B | 109.1 |
C6—C7—H7 | 120.1 | O3—C24—H24B | 109.1 |
O5—C8—C7 | 124.0 (2) | H24A—C24—H24B | 107.8 |
O5—C8—C9 | 115.6 (2) | C24—C25—H25A | 109.5 |
C7—C8—C9 | 120.4 (2) | C24—C25—H25B | 109.5 |
C4—C9—C8 | 119.5 (2) | H25A—C25—H25B | 109.5 |
C4—C9—Cl1 | 120.64 (19) | C24—C25—H25C | 109.5 |
C8—C9—Cl1 | 119.82 (19) | H25A—C25—H25C | 109.5 |
C15—C10—C11 | 119.0 (2) | H25B—C25—H25C | 109.5 |
C15—C10—C3 | 119.3 (2) | O2—C26—C27 | 108.9 (2) |
C11—C10—C3 | 121.7 (2) | O2—C26—H26A | 109.9 |
C10—C11—C12 | 120.1 (3) | C27—C26—H26A | 109.9 |
C10—C11—H11 | 120.0 | O2—C26—H26B | 109.9 |
C12—C11—H11 | 120.0 | C27—C26—H26B | 109.9 |
C13—C12—C11 | 119.7 (3) | H26A—C26—H26B | 108.3 |
C13—C12—H12 | 120.2 | C26—C27—H27A | 109.5 |
C11—C12—H12 | 120.2 | C26—C27—H27B | 109.5 |
C12—C13—C14 | 121.3 (3) | H27A—C27—H27B | 109.5 |
C12—C13—Cl2 | 119.5 (3) | C26—C27—H27C | 109.5 |
C14—C13—Cl2 | 119.2 (2) | H27A—C27—H27C | 109.5 |
C13—C14—C15 | 118.8 (3) | H27B—C27—H27C | 109.5 |
| | | |
C2—S1—N1—N2 | −6.43 (18) | C23—O5—C8—C7 | −5.7 (4) |
C2—S1—N1—C16 | 132.2 (2) | C23—O5—C8—C9 | 174.4 (2) |
C16—N1—N2—C1 | −139.9 (2) | C6—C7—C8—O5 | 179.7 (2) |
S1—N1—N2—C1 | 2.1 (3) | C6—C7—C8—C9 | −0.4 (4) |
N1—N2—C1—C5 | −173.7 (2) | O1—C4—C9—C8 | 177.0 (2) |
N1—N2—C1—C2 | 5.0 (3) | C5—C4—C9—C8 | −1.6 (4) |
C26—O2—C2—C1 | −56.6 (3) | O1—C4—C9—Cl1 | −3.6 (3) |
C26—O2—C2—C3 | −173.0 (2) | C5—C4—C9—Cl1 | 177.8 (2) |
C26—O2—C2—S1 | 60.6 (2) | O5—C8—C9—C4 | −179.0 (2) |
N2—C1—C2—O2 | 114.8 (2) | C7—C8—C9—C4 | 1.1 (4) |
C5—C1—C2—O2 | −66.4 (2) | O5—C8—C9—Cl1 | 1.6 (3) |
N2—C1—C2—C3 | −129.4 (2) | C7—C8—C9—Cl1 | −178.3 (2) |
C5—C1—C2—C3 | 49.4 (3) | O3—C3—C10—C15 | 27.2 (3) |
N2—C1—C2—S1 | −9.2 (3) | O1—C3—C10—C15 | 148.8 (2) |
C5—C1—C2—S1 | 169.64 (17) | C2—C3—C10—C15 | −93.0 (3) |
N1—S1—C2—O2 | −114.93 (16) | O3—C3—C10—C11 | −154.9 (2) |
N1—S1—C2—C1 | 7.88 (16) | O1—C3—C10—C11 | −33.3 (3) |
N1—S1—C2—C3 | 123.12 (17) | C2—C3—C10—C11 | 84.9 (3) |
C24—O3—C3—O1 | −54.8 (3) | C15—C10—C11—C12 | −1.6 (4) |
C24—O3—C3—C10 | 64.5 (3) | C3—C10—C11—C12 | −179.5 (2) |
C24—O3—C3—C2 | −170.1 (2) | C10—C11—C12—C13 | 0.0 (4) |
C4—O1—C3—O3 | −65.4 (3) | C11—C12—C13—C14 | 2.0 (4) |
C4—O1—C3—C10 | 170.74 (19) | C11—C12—C13—Cl2 | −178.3 (2) |
C4—O1—C3—C2 | 48.2 (3) | C12—C13—C14—C15 | −2.4 (4) |
O2—C2—C3—O3 | 176.19 (17) | Cl2—C13—C14—C15 | 177.9 (2) |
C1—C2—C3—O3 | 55.7 (2) | C11—C10—C15—C14 | 1.2 (4) |
S1—C2—C3—O3 | −57.1 (2) | C3—C10—C15—C14 | 179.2 (2) |
O2—C2—C3—O1 | 58.9 (2) | C13—C14—C15—C10 | 0.7 (4) |
C1—C2—C3—O1 | −61.5 (2) | N2—N1—C16—C21 | 6.4 (3) |
S1—C2—C3—O1 | −174.33 (15) | S1—N1—C16—C21 | −131.8 (2) |
O2—C2—C3—C10 | −58.7 (2) | N2—N1—C16—C17 | −168.2 (2) |
C1—C2—C3—C10 | −179.1 (2) | S1—N1—C16—C17 | 53.6 (3) |
S1—C2—C3—C10 | 68.1 (2) | C21—C16—C17—C18 | 2.1 (4) |
C3—O1—C4—C9 | 163.1 (2) | N1—C16—C17—C18 | 176.8 (2) |
C3—O1—C4—C5 | −18.3 (3) | C21—C16—C17—Cl3 | −174.62 (19) |
O1—C4—C5—C6 | −177.2 (2) | N1—C16—C17—Cl3 | 0.1 (3) |
C9—C4—C5—C6 | 1.3 (4) | C16—C17—C18—C19 | −1.2 (4) |
O1—C4—C5—C1 | 2.4 (4) | Cl3—C17—C18—C19 | 175.57 (19) |
C9—C4—C5—C1 | −179.0 (2) | C17—C18—C19—C20 | −1.0 (4) |
N2—C1—C5—C4 | 158.5 (2) | C17—C18—C19—N3 | −179.2 (2) |
C2—C1—C5—C4 | −20.2 (3) | O6—N3—C19—C18 | 13.9 (4) |
N2—C1—C5—C6 | −21.9 (4) | O7—N3—C19—C18 | −165.4 (2) |
C2—C1—C5—C6 | 159.4 (2) | O6—N3—C19—C20 | −164.3 (2) |
C22—O4—C6—C7 | 1.3 (4) | O7—N3—C19—C20 | 16.4 (4) |
C22—O4—C6—C5 | −176.5 (2) | C18—C19—C20—C21 | 2.1 (4) |
C4—C5—C6—O4 | 177.2 (2) | N3—C19—C20—C21 | −179.7 (2) |
C1—C5—C6—O4 | −2.4 (3) | C19—C20—C21—C16 | −1.1 (4) |
C4—C5—C6—C7 | −0.6 (4) | C17—C16—C21—C20 | −0.9 (4) |
C1—C5—C6—C7 | 179.8 (2) | N1—C16—C21—C20 | −175.7 (2) |
O4—C6—C7—C8 | −177.5 (2) | C3—O3—C24—C25 | 122.6 (3) |
C5—C6—C7—C8 | 0.2 (4) | C2—O2—C26—C27 | −174.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25C···O7i | 0.98 | 2.50 | 3.456 (5) | 175 |
Symmetry code: (i) −x+1, −y, −z+1. |