The title compound, C
23H
21NO
5S, was synthesized by the Reformatsky reaction of
N-[(3,4-methylenedioxyphenyl)methylene]-4-methylbenzenesulfonamide and 2-bromoacetophenone. The S atom in the sulfonyl group has a distorted tetrahedral geometry. The two independent molecules in the asymmetric unit form two centrosymmetric dimers connected by intermolecular N—H
O hydrogen bonds between the amino and sulfonyl groups.
Supporting information
CCDC reference: 248807
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.062
- wR factor = 0.147
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.93 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.48 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.60 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.82 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O4
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C19
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C42
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C17
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C20
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C40
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C43
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 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; 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.
3-(3,4-methylenedioxyphenyl)-1-phenyl-3-(
p-toluenesulfonylamino)propan-1-one
top
Crystal data top
C23H21NO5S | F(000) = 1776 |
Mr = 423.48 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/n | Melting point: 397 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 15.968 (5) Å | Cell parameters from 796 reflections |
b = 12.342 (4) Å | θ = 3.3–21.7° |
c = 21.607 (7) Å | µ = 0.19 mm−1 |
β = 105.682 (6)° | T = 293 K |
V = 4100 (2) Å3 | Prism, yellow |
Z = 8 | 0.26 × 0.24 × 0.18 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 8458 independent reflections |
Radiation source: fine-focus sealed tube | 3849 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
ψ and ω scans | θmax = 26.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→20 |
Tmin = 0.951, Tmax = 0.966 | k = −15→15 |
23196 measured reflections | l = −27→16 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0583P)2 + 0.3065P] where P = (Fo2 + 2Fc2)/3 |
8458 reflections | (Δ/σ)max = 0.002 |
543 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.29 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 | 0.07368 (5) | 0.33544 (7) | 0.04848 (4) | 0.0477 (3) | |
S2 | 0.57285 (5) | 0.83492 (7) | 0.02604 (4) | 0.0542 (3) | |
O1 | 0.05041 (14) | 0.36571 (18) | −0.01838 (10) | 0.0635 (7) | |
O2 | 0.04668 (13) | 0.23314 (17) | 0.06657 (11) | 0.0600 (7) | |
O3 | −0.07545 (14) | 0.2821 (2) | 0.17577 (13) | 0.0748 (8) | |
O4 | 0.34584 (14) | 0.53347 (18) | 0.27424 (13) | 0.0719 (8) | |
O5 | 0.32689 (14) | 0.71521 (17) | 0.25292 (12) | 0.0650 (7) | |
O6 | 0.53627 (15) | 0.88317 (19) | −0.03591 (11) | 0.0729 (8) | |
O7 | 0.56711 (14) | 0.72135 (17) | 0.03300 (13) | 0.0734 (8) | |
O8 | 0.42252 (15) | 0.6965 (2) | 0.12456 (14) | 0.0818 (9) | |
O9 | 0.83865 (14) | 0.96593 (18) | 0.27777 (13) | 0.0742 (8) | |
O10 | 0.80402 (14) | 1.14483 (18) | 0.28915 (12) | 0.0717 (8) | |
N1 | 0.03255 (15) | 0.4300 (2) | 0.08251 (12) | 0.0481 (7) | |
H1 | 0.0021 | 0.4790 | 0.0582 | 0.058* | |
N2 | 0.52336 (15) | 0.8956 (2) | 0.07242 (13) | 0.0536 (8) | |
H2 | 0.4838 | 0.9424 | 0.0559 | 0.064* | |
C1 | 0.04332 (18) | 0.4385 (2) | 0.15214 (15) | 0.0431 (8) | |
H1A | 0.0606 | 0.3671 | 0.1712 | 0.052* | |
C2 | 0.11520 (18) | 0.5184 (2) | 0.18259 (15) | 0.0422 (8) | |
C3 | 0.19567 (19) | 0.4797 (2) | 0.21824 (15) | 0.0484 (9) | |
H3 | 0.2044 | 0.4063 | 0.2274 | 0.058* | |
C4 | 0.26130 (19) | 0.5528 (3) | 0.23936 (15) | 0.0466 (8) | |
C5 | 0.3905 (2) | 0.6325 (3) | 0.27493 (19) | 0.0654 (11) | |
H5A | 0.4287 | 0.6280 | 0.2470 | 0.079* | |
H5B | 0.4253 | 0.6487 | 0.3181 | 0.079* | |
C6 | 0.2502 (2) | 0.6609 (3) | 0.22737 (16) | 0.0490 (9) | |
C7 | 0.1713 (2) | 0.7022 (3) | 0.19410 (18) | 0.0653 (11) | |
H7 | 0.1631 | 0.7762 | 0.1868 | 0.078* | |
C8 | 0.1040 (2) | 0.6286 (3) | 0.17175 (17) | 0.0574 (10) | |
H8 | 0.0497 | 0.6542 | 0.1488 | 0.069* | |
C9 | −0.04472 (18) | 0.4660 (2) | 0.16245 (17) | 0.0507 (9) | |
H9A | −0.0364 | 0.4940 | 0.2057 | 0.061* | |
H9B | −0.0720 | 0.5224 | 0.1325 | 0.061* | |
C10 | −0.1045 (2) | 0.3683 (3) | 0.15311 (17) | 0.0507 (9) | |
C11 | −0.1981 (2) | 0.3793 (3) | 0.11828 (16) | 0.0458 (8) | |
C12 | −0.2526 (2) | 0.2920 (3) | 0.11829 (18) | 0.0611 (10) | |
H12 | −0.2303 | 0.2294 | 0.1406 | 0.073* | |
C13 | −0.3390 (2) | 0.2968 (3) | 0.0858 (2) | 0.0714 (12) | |
H13 | −0.3748 | 0.2375 | 0.0864 | 0.086* | |
C14 | −0.3732 (2) | 0.3880 (4) | 0.05262 (19) | 0.0709 (11) | |
H14 | −0.4317 | 0.3904 | 0.0299 | 0.085* | |
C15 | −0.3205 (2) | 0.4762 (3) | 0.05303 (19) | 0.0708 (11) | |
H15 | −0.3437 | 0.5392 | 0.0315 | 0.085* | |
C16 | −0.2336 (2) | 0.4715 (3) | 0.08513 (18) | 0.0614 (10) | |
H16 | −0.1983 | 0.5312 | 0.0845 | 0.074* | |
C17 | 0.18722 (19) | 0.3397 (3) | 0.07862 (15) | 0.0434 (8) | |
C18 | 0.2314 (2) | 0.2483 (3) | 0.1047 (2) | 0.0721 (12) | |
H18 | 0.2016 | 0.1836 | 0.1051 | 0.086* | |
C19 | 0.3203 (2) | 0.2527 (3) | 0.1304 (2) | 0.0907 (15) | |
H19 | 0.3498 | 0.1903 | 0.1481 | 0.109* | |
C20 | 0.3662 (2) | 0.3460 (4) | 0.1305 (2) | 0.0723 (12) | |
C21 | 0.3212 (2) | 0.4363 (3) | 0.1044 (2) | 0.0730 (12) | |
H21 | 0.3511 | 0.5008 | 0.1043 | 0.088* | |
C22 | 0.2314 (2) | 0.4342 (3) | 0.07801 (18) | 0.0650 (11) | |
H22 | 0.2019 | 0.4965 | 0.0601 | 0.078* | |
C23 | 0.4634 (2) | 0.3501 (4) | 0.1606 (3) | 0.125 (2) | |
H23A | 0.4885 | 0.4054 | 0.1400 | 0.187* | |
H23B | 0.4886 | 0.2812 | 0.1554 | 0.187* | |
H23C | 0.4748 | 0.3663 | 0.2056 | 0.187* | |
C24 | 0.54375 (19) | 0.8734 (3) | 0.14196 (16) | 0.0510 (9) | |
H24 | 0.5677 | 0.7999 | 0.1493 | 0.061* | |
C25 | 0.61130 (19) | 0.9508 (2) | 0.18120 (15) | 0.0442 (8) | |
C26 | 0.69418 (19) | 0.9126 (3) | 0.21171 (16) | 0.0503 (9) | |
H26 | 0.7083 | 0.8399 | 0.2092 | 0.060* | |
C27 | 0.75394 (19) | 0.9844 (3) | 0.24525 (16) | 0.0479 (9) | |
C28 | 0.8739 (2) | 1.0695 (3) | 0.2988 (2) | 0.0817 (13) | |
H28A | 0.9139 | 1.0916 | 0.2745 | 0.098* | |
H28B | 0.9054 | 1.0667 | 0.3439 | 0.098* | |
C29 | 0.73308 (19) | 1.0911 (3) | 0.25113 (16) | 0.0485 (9) | |
C30 | 0.6532 (2) | 1.1316 (3) | 0.22271 (17) | 0.0543 (9) | |
H30 | 0.6399 | 1.2042 | 0.2266 | 0.065* | |
C31 | 0.5918 (2) | 1.0589 (3) | 0.18720 (16) | 0.0507 (9) | |
H31 | 0.5362 | 1.0838 | 0.1670 | 0.061* | |
C32 | 0.4592 (2) | 0.8748 (3) | 0.16141 (18) | 0.0669 (11) | |
H32A | 0.4322 | 0.9455 | 0.1518 | 0.080* | |
H32B | 0.4718 | 0.8633 | 0.2074 | 0.080* | |
C33 | 0.3957 (2) | 0.7880 (3) | 0.12655 (18) | 0.0603 (10) | |
C34 | 0.3034 (2) | 0.8154 (3) | 0.09566 (17) | 0.0530 (9) | |
C35 | 0.2644 (2) | 0.9113 (3) | 0.10846 (18) | 0.0660 (11) | |
H35 | 0.2975 | 0.9628 | 0.1359 | 0.079* | |
C36 | 0.1770 (2) | 0.9299 (3) | 0.0806 (2) | 0.0755 (12) | |
H36 | 0.1515 | 0.9936 | 0.0897 | 0.091* | |
C37 | 0.1278 (2) | 0.8553 (3) | 0.03999 (19) | 0.0774 (12) | |
H37 | 0.0689 | 0.8681 | 0.0214 | 0.093* | |
C38 | 0.1654 (2) | 0.7611 (3) | 0.02657 (19) | 0.0719 (12) | |
H38 | 0.1319 | 0.7106 | −0.0013 | 0.086* | |
C39 | 0.2521 (2) | 0.7412 (3) | 0.05401 (18) | 0.0620 (10) | |
H39 | 0.2767 | 0.6771 | 0.0446 | 0.074* | |
C40 | 0.6835 (2) | 0.8697 (3) | 0.05252 (16) | 0.0508 (9) | |
C41 | 0.7448 (2) | 0.7916 (3) | 0.0750 (2) | 0.0792 (13) | |
H41 | 0.7286 | 0.7192 | 0.0750 | 0.095* | |
C42 | 0.8313 (3) | 0.8210 (4) | 0.0977 (2) | 0.0999 (16) | |
H42 | 0.8729 | 0.7674 | 0.1123 | 0.120* | |
C43 | 0.8570 (3) | 0.9255 (4) | 0.0993 (2) | 0.0891 (14) | |
C44 | 0.7947 (3) | 1.0029 (4) | 0.0765 (2) | 0.0908 (14) | |
H44 | 0.8112 | 1.0752 | 0.0772 | 0.109* | |
C45 | 0.7084 (3) | 0.9763 (3) | 0.05253 (19) | 0.0722 (11) | |
H45 | 0.6673 | 1.0299 | 0.0365 | 0.087* | |
C46 | 0.9513 (3) | 0.9571 (5) | 0.1248 (3) | 0.153 (3) | |
H46A | 0.9865 | 0.8930 | 0.1338 | 0.229* | |
H46B | 0.9588 | 0.9985 | 0.1635 | 0.229* | |
H46C | 0.9686 | 1.0000 | 0.0933 | 0.229* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0421 (5) | 0.0461 (5) | 0.0480 (6) | −0.0024 (4) | 0.0005 (4) | −0.0060 (5) |
S2 | 0.0502 (5) | 0.0471 (5) | 0.0554 (6) | 0.0034 (4) | −0.0027 (5) | −0.0074 (5) |
O1 | 0.0688 (15) | 0.0716 (17) | 0.0398 (15) | 0.0124 (12) | −0.0028 (12) | −0.0052 (13) |
O2 | 0.0509 (14) | 0.0468 (14) | 0.0743 (18) | −0.0118 (11) | 0.0032 (13) | −0.0066 (12) |
O3 | 0.0537 (15) | 0.0565 (16) | 0.112 (2) | 0.0045 (12) | 0.0186 (15) | 0.0262 (16) |
O4 | 0.0474 (14) | 0.0523 (15) | 0.094 (2) | −0.0025 (11) | −0.0185 (13) | 0.0076 (14) |
O5 | 0.0521 (14) | 0.0438 (14) | 0.0861 (19) | −0.0080 (12) | −0.0033 (13) | −0.0052 (13) |
O6 | 0.0820 (18) | 0.0720 (17) | 0.0503 (17) | 0.0195 (13) | −0.0069 (13) | −0.0060 (14) |
O7 | 0.0609 (15) | 0.0434 (15) | 0.101 (2) | −0.0024 (11) | −0.0047 (14) | −0.0133 (14) |
O8 | 0.0564 (16) | 0.0673 (19) | 0.115 (3) | −0.0120 (14) | 0.0113 (16) | −0.0066 (17) |
O9 | 0.0448 (14) | 0.0559 (16) | 0.101 (2) | 0.0020 (12) | −0.0170 (13) | −0.0030 (14) |
O10 | 0.0526 (15) | 0.0488 (15) | 0.095 (2) | −0.0106 (12) | −0.0127 (14) | −0.0090 (14) |
N1 | 0.0418 (15) | 0.0515 (17) | 0.0434 (18) | 0.0087 (12) | −0.0017 (13) | 0.0017 (14) |
N2 | 0.0376 (15) | 0.0599 (18) | 0.054 (2) | 0.0077 (13) | −0.0036 (14) | 0.0010 (15) |
C1 | 0.0393 (18) | 0.0439 (19) | 0.042 (2) | −0.0004 (14) | 0.0030 (15) | 0.0011 (16) |
C2 | 0.0389 (18) | 0.043 (2) | 0.041 (2) | −0.0008 (15) | 0.0042 (15) | 0.0042 (16) |
C3 | 0.048 (2) | 0.0372 (18) | 0.052 (2) | −0.0027 (16) | 0.0014 (17) | 0.0055 (17) |
C4 | 0.043 (2) | 0.047 (2) | 0.042 (2) | −0.0007 (16) | −0.0029 (16) | 0.0011 (17) |
C5 | 0.049 (2) | 0.051 (2) | 0.085 (3) | −0.0063 (18) | 0.000 (2) | −0.003 (2) |
C6 | 0.048 (2) | 0.040 (2) | 0.052 (2) | −0.0066 (17) | 0.0014 (17) | −0.0055 (18) |
C7 | 0.057 (2) | 0.038 (2) | 0.088 (3) | 0.0022 (17) | −0.002 (2) | 0.004 (2) |
C8 | 0.043 (2) | 0.045 (2) | 0.073 (3) | 0.0053 (16) | −0.0025 (18) | 0.0016 (19) |
C9 | 0.0438 (19) | 0.048 (2) | 0.059 (2) | 0.0002 (16) | 0.0115 (17) | −0.0004 (18) |
C10 | 0.046 (2) | 0.051 (2) | 0.058 (2) | 0.0040 (17) | 0.0188 (18) | 0.0029 (19) |
C11 | 0.0452 (19) | 0.045 (2) | 0.049 (2) | −0.0038 (16) | 0.0146 (17) | −0.0056 (17) |
C12 | 0.057 (2) | 0.059 (2) | 0.071 (3) | −0.0060 (19) | 0.023 (2) | 0.006 (2) |
C13 | 0.060 (3) | 0.072 (3) | 0.084 (3) | −0.024 (2) | 0.021 (2) | −0.004 (2) |
C14 | 0.046 (2) | 0.090 (3) | 0.071 (3) | −0.008 (2) | 0.006 (2) | −0.010 (3) |
C15 | 0.061 (3) | 0.060 (3) | 0.082 (3) | 0.009 (2) | 0.003 (2) | −0.001 (2) |
C16 | 0.051 (2) | 0.051 (2) | 0.077 (3) | −0.0020 (17) | 0.009 (2) | 0.000 (2) |
C17 | 0.0441 (18) | 0.0438 (19) | 0.041 (2) | −0.0027 (16) | 0.0094 (15) | −0.0015 (17) |
C18 | 0.046 (2) | 0.049 (2) | 0.115 (4) | −0.0019 (17) | 0.011 (2) | 0.001 (2) |
C19 | 0.054 (3) | 0.067 (3) | 0.143 (5) | 0.017 (2) | 0.012 (3) | 0.011 (3) |
C20 | 0.044 (2) | 0.088 (3) | 0.084 (3) | 0.001 (2) | 0.014 (2) | −0.012 (3) |
C21 | 0.058 (3) | 0.071 (3) | 0.094 (3) | −0.025 (2) | 0.026 (2) | −0.007 (2) |
C22 | 0.056 (2) | 0.057 (2) | 0.081 (3) | −0.0051 (19) | 0.016 (2) | 0.012 (2) |
C23 | 0.041 (2) | 0.146 (5) | 0.176 (5) | −0.001 (3) | 0.012 (3) | −0.027 (4) |
C24 | 0.043 (2) | 0.050 (2) | 0.052 (2) | −0.0093 (15) | −0.0004 (17) | 0.0038 (18) |
C25 | 0.0398 (19) | 0.044 (2) | 0.043 (2) | −0.0088 (15) | 0.0021 (16) | 0.0019 (16) |
C26 | 0.046 (2) | 0.0384 (19) | 0.059 (2) | −0.0015 (16) | 0.0021 (18) | 0.0016 (17) |
C27 | 0.0396 (19) | 0.044 (2) | 0.054 (2) | −0.0032 (15) | 0.0019 (17) | 0.0044 (18) |
C28 | 0.050 (2) | 0.068 (3) | 0.110 (4) | −0.008 (2) | −0.009 (2) | −0.005 (3) |
C29 | 0.041 (2) | 0.046 (2) | 0.052 (2) | −0.0117 (16) | 0.0005 (17) | 0.0033 (17) |
C30 | 0.051 (2) | 0.0364 (19) | 0.069 (3) | −0.0036 (16) | 0.0054 (19) | 0.0031 (18) |
C31 | 0.0388 (18) | 0.049 (2) | 0.058 (2) | −0.0027 (16) | 0.0016 (17) | 0.0051 (18) |
C32 | 0.050 (2) | 0.077 (3) | 0.069 (3) | −0.0268 (19) | 0.008 (2) | −0.017 (2) |
C33 | 0.056 (2) | 0.062 (3) | 0.065 (3) | −0.020 (2) | 0.020 (2) | −0.008 (2) |
C34 | 0.047 (2) | 0.060 (2) | 0.052 (2) | −0.0205 (18) | 0.0138 (18) | −0.0053 (19) |
C35 | 0.066 (3) | 0.064 (3) | 0.064 (3) | −0.021 (2) | 0.010 (2) | −0.018 (2) |
C36 | 0.060 (3) | 0.070 (3) | 0.089 (3) | −0.002 (2) | 0.007 (2) | −0.024 (2) |
C37 | 0.056 (2) | 0.088 (3) | 0.080 (3) | −0.009 (2) | 0.004 (2) | −0.020 (3) |
C38 | 0.050 (2) | 0.087 (3) | 0.074 (3) | −0.020 (2) | 0.009 (2) | −0.031 (2) |
C39 | 0.057 (2) | 0.065 (2) | 0.066 (3) | −0.0186 (19) | 0.019 (2) | −0.021 (2) |
C40 | 0.053 (2) | 0.048 (2) | 0.050 (2) | −0.0008 (17) | 0.0126 (18) | −0.0063 (18) |
C41 | 0.055 (2) | 0.051 (2) | 0.119 (4) | 0.0043 (19) | 0.003 (2) | −0.012 (2) |
C42 | 0.050 (3) | 0.099 (4) | 0.138 (5) | 0.013 (2) | 0.004 (3) | −0.031 (3) |
C43 | 0.060 (3) | 0.105 (4) | 0.110 (4) | −0.026 (3) | 0.037 (3) | −0.034 (3) |
C44 | 0.089 (3) | 0.076 (3) | 0.119 (4) | −0.034 (3) | 0.048 (3) | −0.014 (3) |
C45 | 0.077 (3) | 0.057 (3) | 0.086 (3) | −0.005 (2) | 0.028 (2) | 0.012 (2) |
C46 | 0.064 (3) | 0.204 (6) | 0.190 (6) | −0.058 (3) | 0.034 (4) | −0.065 (5) |
Geometric parameters (Å, º) top
S1—O2 | 1.423 (2) | C18—H18 | 0.9300 |
S1—O1 | 1.440 (2) | C19—C20 | 1.364 (5) |
S1—N1 | 1.611 (3) | C19—H19 | 0.9300 |
S1—C17 | 1.754 (3) | C20—C21 | 1.363 (5) |
S2—O7 | 1.415 (2) | C20—C23 | 1.513 (5) |
S2—O6 | 1.437 (2) | C21—C22 | 1.392 (5) |
S2—N2 | 1.618 (3) | C21—H21 | 0.9300 |
S2—C40 | 1.757 (3) | C22—H22 | 0.9300 |
O3—C10 | 1.210 (4) | C23—H23A | 0.9600 |
O4—C4 | 1.378 (3) | C23—H23B | 0.9600 |
O4—C5 | 1.413 (4) | C23—H23C | 0.9600 |
O5—C6 | 1.374 (3) | C24—C25 | 1.517 (4) |
O5—C5 | 1.427 (4) | C24—C32 | 1.519 (4) |
O8—C33 | 1.213 (4) | C24—H24 | 0.9800 |
O9—C27 | 1.364 (3) | C25—C31 | 1.384 (4) |
O9—C28 | 1.420 (4) | C25—C26 | 1.392 (4) |
O10—C29 | 1.377 (3) | C26—C27 | 1.359 (4) |
O10—C28 | 1.424 (4) | C26—H26 | 0.9300 |
N1—C1 | 1.471 (4) | C27—C29 | 1.372 (4) |
N1—H1 | 0.8600 | C28—H28A | 0.9700 |
N2—C24 | 1.475 (4) | C28—H28B | 0.9700 |
N2—H2 | 0.8600 | C29—C30 | 1.353 (4) |
C1—C9 | 1.520 (4) | C30—C31 | 1.396 (4) |
C1—C2 | 1.521 (4) | C30—H30 | 0.9300 |
C1—H1A | 0.9800 | C31—H31 | 0.9300 |
C2—C8 | 1.383 (4) | C32—C33 | 1.527 (4) |
C2—C3 | 1.392 (4) | C32—H32A | 0.9700 |
C3—C4 | 1.365 (4) | C32—H32B | 0.9700 |
C3—H3 | 0.9300 | C33—C34 | 1.483 (5) |
C4—C6 | 1.361 (4) | C34—C39 | 1.386 (4) |
C5—H5A | 0.9700 | C34—C35 | 1.399 (5) |
C5—H5B | 0.9700 | C35—C36 | 1.382 (5) |
C6—C7 | 1.369 (4) | C35—H35 | 0.9300 |
C7—C8 | 1.391 (4) | C36—C37 | 1.365 (5) |
C7—H7 | 0.9300 | C36—H36 | 0.9300 |
C8—H8 | 0.9300 | C37—C38 | 1.375 (5) |
C9—C10 | 1.517 (4) | C37—H37 | 0.9300 |
C9—H9A | 0.9700 | C38—C39 | 1.372 (5) |
C9—H9B | 0.9700 | C38—H38 | 0.9300 |
C10—C11 | 1.486 (4) | C39—H39 | 0.9300 |
C11—C16 | 1.382 (4) | C40—C41 | 1.367 (5) |
C11—C12 | 1.386 (4) | C40—C45 | 1.374 (4) |
C12—C13 | 1.370 (5) | C41—C42 | 1.383 (5) |
C12—H12 | 0.9300 | C41—H41 | 0.9300 |
C13—C14 | 1.367 (5) | C42—C43 | 1.351 (6) |
C13—H13 | 0.9300 | C42—H42 | 0.9300 |
C14—C15 | 1.374 (5) | C43—C44 | 1.372 (6) |
C14—H14 | 0.9300 | C43—C46 | 1.508 (5) |
C15—C16 | 1.374 (4) | C44—C45 | 1.374 (5) |
C15—H15 | 0.9300 | C44—H44 | 0.9300 |
C16—H16 | 0.9300 | C45—H45 | 0.9300 |
C17—C22 | 1.365 (4) | C46—H46A | 0.9600 |
C17—C18 | 1.369 (4) | C46—H46B | 0.9600 |
C18—C19 | 1.378 (5) | C46—H46C | 0.9600 |
| | | |
O2—S1—O1 | 119.38 (14) | C20—C21—H21 | 119.2 |
O2—S1—N1 | 109.04 (14) | C22—C21—H21 | 119.2 |
O1—S1—N1 | 104.09 (13) | C17—C22—C21 | 119.3 (3) |
O2—S1—C17 | 106.52 (14) | C17—C22—H22 | 120.3 |
O1—S1—C17 | 108.98 (15) | C21—C22—H22 | 120.3 |
N1—S1—C17 | 108.46 (14) | C20—C23—H23A | 109.5 |
O7—S2—O6 | 119.19 (15) | C20—C23—H23B | 109.5 |
O7—S2—N2 | 109.63 (16) | H23A—C23—H23B | 109.5 |
O6—S2—N2 | 103.99 (14) | C20—C23—H23C | 109.5 |
O7—S2—C40 | 107.21 (15) | H23A—C23—H23C | 109.5 |
O6—S2—C40 | 108.78 (16) | H23B—C23—H23C | 109.5 |
N2—S2—C40 | 107.56 (15) | N2—C24—C25 | 112.4 (3) |
C4—O4—C5 | 105.8 (2) | N2—C24—C32 | 108.2 (3) |
C6—O5—C5 | 105.2 (2) | C25—C24—C32 | 112.9 (3) |
C27—O9—C28 | 105.4 (2) | N2—C24—H24 | 107.7 |
C29—O10—C28 | 105.0 (2) | C25—C24—H24 | 107.7 |
C1—N1—S1 | 124.7 (2) | C32—C24—H24 | 107.7 |
C1—N1—H1 | 117.7 | C31—C25—C26 | 119.4 (3) |
S1—N1—H1 | 117.7 | C31—C25—C24 | 121.0 (3) |
C24—N2—S2 | 122.3 (2) | C26—C25—C24 | 119.5 (3) |
C24—N2—H2 | 118.8 | C27—C26—C25 | 118.2 (3) |
S2—N2—H2 | 118.8 | C27—C26—H26 | 120.9 |
N1—C1—C9 | 108.0 (2) | C25—C26—H26 | 120.9 |
N1—C1—C2 | 110.8 (3) | C26—C27—O9 | 128.4 (3) |
C9—C1—C2 | 114.3 (3) | C26—C27—C29 | 121.5 (3) |
N1—C1—H1A | 107.9 | O9—C27—C29 | 110.1 (3) |
C9—C1—H1A | 107.9 | O9—C28—O10 | 108.3 (3) |
C2—C1—H1A | 107.9 | O9—C28—H28A | 110.0 |
C8—C2—C3 | 119.2 (3) | O10—C28—H28A | 110.0 |
C8—C2—C1 | 121.1 (3) | O9—C28—H28B | 110.0 |
C3—C2—C1 | 119.5 (3) | O10—C28—H28B | 110.0 |
C4—C3—C2 | 118.0 (3) | H28A—C28—H28B | 108.4 |
C4—C3—H3 | 121.0 | C30—C29—C27 | 122.4 (3) |
C2—C3—H3 | 121.0 | C30—C29—O10 | 128.0 (3) |
C6—C4—C3 | 122.4 (3) | C27—C29—O10 | 109.7 (3) |
C6—C4—O4 | 109.4 (3) | C29—C30—C31 | 116.6 (3) |
C3—C4—O4 | 128.2 (3) | C29—C30—H30 | 121.7 |
O4—C5—O5 | 107.7 (2) | C31—C30—H30 | 121.7 |
O4—C5—H5A | 110.2 | C25—C31—C30 | 121.9 (3) |
O5—C5—H5A | 110.2 | C25—C31—H31 | 119.0 |
O4—C5—H5B | 110.2 | C30—C31—H31 | 119.0 |
O5—C5—H5B | 110.2 | C24—C32—C33 | 112.1 (3) |
H5A—C5—H5B | 108.5 | C24—C32—H32A | 109.2 |
C4—C6—C7 | 121.3 (3) | C33—C32—H32A | 109.2 |
C4—C6—O5 | 110.2 (3) | C24—C32—H32B | 109.2 |
C7—C6—O5 | 128.5 (3) | C33—C32—H32B | 109.2 |
C6—C7—C8 | 117.0 (3) | H32A—C32—H32B | 107.9 |
C6—C7—H7 | 121.5 | O8—C33—C34 | 120.9 (3) |
C8—C7—H7 | 121.5 | O8—C33—C32 | 118.5 (3) |
C2—C8—C7 | 122.1 (3) | C34—C33—C32 | 120.5 (3) |
C2—C8—H8 | 119.0 | C39—C34—C35 | 118.1 (3) |
C7—C8—H8 | 119.0 | C39—C34—C33 | 118.8 (3) |
C10—C9—C1 | 112.1 (3) | C35—C34—C33 | 123.0 (3) |
C10—C9—H9A | 109.2 | C36—C35—C34 | 120.4 (3) |
C1—C9—H9A | 109.2 | C36—C35—H35 | 119.8 |
C10—C9—H9B | 109.2 | C34—C35—H35 | 119.8 |
C1—C9—H9B | 109.2 | C37—C36—C35 | 120.4 (4) |
H9A—C9—H9B | 107.9 | C37—C36—H36 | 119.8 |
O3—C10—C11 | 120.6 (3) | C35—C36—H36 | 119.8 |
O3—C10—C9 | 119.0 (3) | C36—C37—C38 | 119.8 (4) |
C11—C10—C9 | 120.3 (3) | C36—C37—H37 | 120.1 |
C16—C11—C12 | 118.0 (3) | C38—C37—H37 | 120.1 |
C16—C11—C10 | 123.6 (3) | C39—C38—C37 | 120.5 (3) |
C12—C11—C10 | 118.3 (3) | C39—C38—H38 | 119.7 |
C13—C12—C11 | 120.9 (4) | C37—C38—H38 | 119.7 |
C13—C12—H12 | 119.6 | C38—C39—C34 | 120.8 (4) |
C11—C12—H12 | 119.6 | C38—C39—H39 | 119.6 |
C14—C13—C12 | 120.6 (3) | C34—C39—H39 | 119.6 |
C14—C13—H13 | 119.7 | C41—C40—C45 | 119.7 (3) |
C12—C13—H13 | 119.7 | C41—C40—S2 | 120.3 (3) |
C13—C14—C15 | 119.5 (3) | C45—C40—S2 | 120.0 (3) |
C13—C14—H14 | 120.3 | C40—C41—C42 | 119.4 (4) |
C15—C14—H14 | 120.3 | C40—C41—H41 | 120.3 |
C16—C15—C14 | 120.2 (4) | C42—C41—H41 | 120.3 |
C16—C15—H15 | 119.9 | C43—C42—C41 | 121.8 (4) |
C14—C15—H15 | 119.9 | C43—C42—H42 | 119.1 |
C15—C16—C11 | 120.9 (3) | C41—C42—H42 | 119.1 |
C15—C16—H16 | 119.5 | C42—C43—C44 | 118.0 (4) |
C11—C16—H16 | 119.5 | C42—C43—C46 | 121.5 (5) |
C22—C17—C18 | 119.8 (3) | C44—C43—C46 | 120.5 (5) |
C22—C17—S1 | 120.5 (3) | C43—C44—C45 | 121.7 (4) |
C18—C17—S1 | 119.6 (3) | C43—C44—H44 | 119.1 |
C17—C18—C19 | 119.5 (3) | C45—C44—H44 | 119.1 |
C17—C18—H18 | 120.2 | C44—C45—C40 | 119.3 (4) |
C19—C18—H18 | 120.2 | C44—C45—H45 | 120.4 |
C20—C19—C18 | 121.9 (4) | C40—C45—H45 | 120.4 |
C20—C19—H19 | 119.1 | C43—C46—H46A | 109.5 |
C18—C19—H19 | 119.1 | C43—C46—H46B | 109.5 |
C21—C20—C19 | 117.8 (3) | H46A—C46—H46B | 109.5 |
C21—C20—C23 | 121.0 (4) | C43—C46—H46C | 109.5 |
C19—C20—C23 | 121.2 (4) | H46A—C46—H46C | 109.5 |
C20—C21—C22 | 121.6 (3) | H46B—C46—H46C | 109.5 |
| | | |
O2—S1—N1—C1 | 55.2 (3) | C18—C17—C22—C21 | −0.4 (6) |
O1—S1—N1—C1 | −176.3 (2) | S1—C17—C22—C21 | 177.6 (3) |
C17—S1—N1—C1 | −60.4 (3) | C20—C21—C22—C17 | 0.5 (6) |
O7—S2—N2—C24 | 53.9 (3) | S2—N2—C24—C25 | 93.1 (3) |
O6—S2—N2—C24 | −177.6 (2) | S2—N2—C24—C32 | −141.7 (2) |
C40—S2—N2—C24 | −62.4 (3) | N2—C24—C25—C31 | 69.9 (4) |
S1—N1—C1—C9 | −135.8 (2) | C32—C24—C25—C31 | −52.8 (4) |
S1—N1—C1—C2 | 98.4 (3) | N2—C24—C25—C26 | −110.2 (3) |
N1—C1—C2—C8 | 71.0 (4) | C32—C24—C25—C26 | 127.1 (3) |
C9—C1—C2—C8 | −51.2 (4) | C31—C25—C26—C27 | −1.6 (5) |
N1—C1—C2—C3 | −104.4 (3) | C24—C25—C26—C27 | 178.4 (3) |
C9—C1—C2—C3 | 133.4 (3) | C25—C26—C27—O9 | −178.9 (3) |
C8—C2—C3—C4 | −2.0 (5) | C25—C26—C27—C29 | 2.3 (5) |
C1—C2—C3—C4 | 173.5 (3) | C28—O9—C27—C26 | 174.5 (4) |
C2—C3—C4—C6 | 0.8 (5) | C28—O9—C27—C29 | −6.5 (4) |
C2—C3—C4—O4 | −179.0 (3) | C27—O9—C28—O10 | 11.6 (4) |
C5—O4—C4—C6 | −8.8 (4) | C29—O10—C28—O9 | −12.3 (4) |
C5—O4—C4—C3 | 171.0 (4) | C26—C27—C29—C30 | −1.9 (6) |
C4—O4—C5—O5 | 13.1 (4) | O9—C27—C29—C30 | 179.1 (3) |
C6—O5—C5—O4 | −12.5 (4) | C26—C27—C29—O10 | 177.8 (3) |
C3—C4—C6—C7 | 1.1 (6) | O9—C27—C29—O10 | −1.2 (4) |
O4—C4—C6—C7 | −179.1 (3) | C28—O10—C29—C30 | −172.0 (4) |
C3—C4—C6—O5 | −178.8 (3) | C28—O10—C29—C27 | 8.3 (4) |
O4—C4—C6—O5 | 1.0 (4) | C27—C29—C30—C31 | 0.7 (5) |
C5—O5—C6—C4 | 7.2 (4) | O10—C29—C30—C31 | −179.0 (3) |
C5—O5—C6—C7 | −172.8 (4) | C26—C25—C31—C30 | 0.5 (5) |
C4—C6—C7—C8 | −1.7 (6) | C24—C25—C31—C30 | −179.5 (3) |
O5—C6—C7—C8 | 178.3 (3) | C29—C30—C31—C25 | 0.0 (5) |
C3—C2—C8—C7 | 1.5 (5) | N2—C24—C32—C33 | 61.2 (4) |
C1—C2—C8—C7 | −173.9 (3) | C25—C24—C32—C33 | −173.8 (3) |
C6—C7—C8—C2 | 0.3 (6) | C24—C32—C33—O8 | 47.5 (5) |
N1—C1—C9—C10 | 76.6 (3) | C24—C32—C33—C34 | −132.2 (3) |
C2—C1—C9—C10 | −159.7 (3) | O8—C33—C34—C39 | −12.4 (6) |
C1—C9—C10—O3 | 43.3 (4) | C32—C33—C34—C39 | 167.4 (3) |
C1—C9—C10—C11 | −138.5 (3) | O8—C33—C34—C35 | 165.0 (4) |
O3—C10—C11—C16 | −172.5 (4) | C32—C33—C34—C35 | −15.2 (5) |
C9—C10—C11—C16 | 9.3 (5) | C39—C34—C35—C36 | 0.7 (6) |
O3—C10—C11—C12 | 6.7 (5) | C33—C34—C35—C36 | −176.7 (4) |
C9—C10—C11—C12 | −171.5 (3) | C34—C35—C36—C37 | −0.5 (6) |
C16—C11—C12—C13 | 0.6 (5) | C35—C36—C37—C38 | −0.1 (7) |
C10—C11—C12—C13 | −178.6 (3) | C36—C37—C38—C39 | 0.4 (7) |
C11—C12—C13—C14 | 0.1 (6) | C37—C38—C39—C34 | −0.1 (6) |
C12—C13—C14—C15 | −1.3 (6) | C35—C34—C39—C38 | −0.4 (6) |
C13—C14—C15—C16 | 1.8 (6) | C33—C34—C39—C38 | 177.1 (3) |
C14—C15—C16—C11 | −1.1 (6) | O7—S2—C40—C41 | −0.5 (4) |
C12—C11—C16—C15 | −0.2 (5) | O6—S2—C40—C41 | −130.7 (3) |
C10—C11—C16—C15 | 179.0 (4) | N2—S2—C40—C41 | 117.3 (3) |
O2—S1—C17—C22 | −169.6 (3) | O7—S2—C40—C45 | −178.6 (3) |
O1—S1—C17—C22 | 60.4 (3) | O6—S2—C40—C45 | 51.3 (3) |
N1—S1—C17—C22 | −52.3 (3) | N2—S2—C40—C45 | −60.7 (3) |
O2—S1—C17—C18 | 8.4 (3) | C45—C40—C41—C42 | 0.3 (6) |
O1—S1—C17—C18 | −121.6 (3) | S2—C40—C41—C42 | −177.8 (3) |
N1—S1—C17—C18 | 125.7 (3) | C40—C41—C42—C43 | 1.0 (8) |
C22—C17—C18—C19 | 0.2 (6) | C41—C42—C43—C44 | −1.1 (8) |
S1—C17—C18—C19 | −177.8 (3) | C41—C42—C43—C46 | 179.3 (5) |
C17—C18—C19—C20 | −0.1 (7) | C42—C43—C44—C45 | −0.1 (8) |
C18—C19—C20—C21 | 0.2 (7) | C46—C43—C44—C45 | 179.6 (4) |
C18—C19—C20—C23 | 178.2 (4) | C43—C44—C45—C40 | 1.3 (7) |
C19—C20—C21—C22 | −0.4 (7) | C41—C40—C45—C44 | −1.4 (6) |
C23—C20—C21—C22 | −178.4 (4) | S2—C40—C45—C44 | 176.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.17 | 3.007 (3) | 163 |
N2—H2···O6ii | 0.86 | 2.20 | 2.929 (4) | 142 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z. |