In the title compound, C
20H
21FN
2O
2S
2, the thiazolidine ring is disordered and both conformers adopt envelope conformations. One of the pyrrolidine rings adopts an envelope conformation, while the other is in a twist conformation. C—H
O hydrogen bonds link the molecules into a chain along the
a axis, and inversion-related molecules in adjacent chains are interconnected
via C—H
O and C—H
π interactions to form a double-stranded chain.
Supporting information
CCDC reference: 621488
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.001 Å
- Disorder in main residue
- R factor = 0.037
- wR factor = 0.100
- Data-to-parameter ratio = 38.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT213_ALERT_2_C Atom C7B has ADP max/min Ratio ............. 3.20 prola
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.20 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.06 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7B
PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
2-(4-Fluorophenyl)-5-(phenylsulfonyl)perhydro-1,3-thiazolo[3,4-
a]pyrrolo[4,5-
c]pyrrole
top
Crystal data top
C20H21FN2O2S2 | F(000) = 848 |
Mr = 404.51 | Dx = 1.440 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9333 reflections |
a = 10.4806 (1) Å | θ = 2.7–36.6° |
b = 10.6106 (1) Å | µ = 0.31 mm−1 |
c = 16.8245 (2) Å | T = 100 K |
β = 94.055 (1)° | Block, colourless |
V = 1866.29 (3) Å3 | 0.48 × 0.42 × 0.30 mm |
Z = 4 | |
Data collection top
Bruker SMART APEXII CCD area-detector diffractometer | 9762 independent reflections |
Radiation source: fine-focus sealed tube | 8289 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 8.33 pixels mm-1 | θmax = 37.5°, θmin = 2.3° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −18→18 |
Tmin = 0.864, Tmax = 0.912 | l = −28→28 |
62572 measured reflections | |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0516P)2 + 0.4746P] where P = (Fo2 + 2Fc2)/3 |
9762 reflections | (Δ/σ)max = 0.001 |
254 parameters | Δρmax = 0.63 e Å−3 |
2 restraints | Δρmin = −0.42 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 | Occ. (<1) |
S1 | −0.11192 (2) | −0.12566 (2) | 0.165581 (15) | 0.02298 (5) | |
S2 | 0.513995 (18) | 0.068797 (18) | 0.181535 (11) | 0.01555 (4) | |
F1 | −0.15167 (6) | 0.40452 (6) | −0.05085 (4) | 0.02827 (12) | |
O1 | 0.59374 (6) | 0.12695 (7) | 0.24431 (4) | 0.02201 (12) | |
O2 | 0.56581 (6) | −0.02464 (6) | 0.13091 (4) | 0.02099 (11) | |
N1 | 0.39763 (6) | 0.00111 (7) | 0.22281 (4) | 0.01597 (11) | |
N2 | 0.09697 (6) | 0.01072 (6) | 0.19583 (4) | 0.01407 (10) | |
C1 | 0.33523 (8) | 0.06010 (8) | 0.28919 (5) | 0.01812 (13) | |
H1A | 0.2962 | 0.1420 | 0.2732 | 0.022* | |
H1B | 0.3965 | 0.0729 | 0.3360 | 0.022* | |
C2 | 0.23299 (8) | −0.03743 (8) | 0.30660 (5) | 0.01931 (14) | |
H2 | 0.2687 | −0.1064 | 0.3421 | 0.023* | |
C3 | 0.19055 (7) | −0.08640 (7) | 0.22291 (5) | 0.01634 (12) | |
H3 | 0.1516 | −0.1723 | 0.2242 | 0.020* | |
C4 | 0.30906 (7) | −0.08322 (7) | 0.17516 (5) | 0.01703 (12) | |
H4A | 0.3461 | −0.1685 | 0.1705 | 0.020* | |
H4B | 0.2886 | −0.0487 | 0.1211 | 0.020* | |
C5 | 0.11189 (9) | 0.02083 (10) | 0.33813 (5) | 0.02348 (16) | |
H5A | 0.0743 | −0.0364 | 0.3766 | 0.028* | |
H5B | 0.1317 | 0.1025 | 0.3646 | 0.028* | |
C6 | 0.01993 (8) | 0.03918 (8) | 0.26388 (5) | 0.01960 (14) | |
H6A | −0.0146 | 0.1270 | 0.2607 | 0.024* | 0.45 (2) |
H6B | 0.0055 | 0.1285 | 0.2609 | 0.024* | 0.55 (2) |
C7A | −0.0899 (5) | −0.0602 (6) | 0.2648 (2) | 0.0260 (9) | 0.45 (2) |
H7AA | −0.1698 | −0.0196 | 0.2797 | 0.031* | 0.45 (2) |
H7AB | −0.0667 | −0.1275 | 0.3040 | 0.031* | 0.45 (2) |
C7B | −0.1077 (5) | −0.0340 (8) | 0.2568 (3) | 0.0462 (14) | 0.55 (2) |
H7BA | −0.1807 | 0.0255 | 0.2551 | 0.055* | 0.55 (2) |
H7BB | −0.1136 | −0.0904 | 0.3033 | 0.055* | 0.55 (2) |
C8 | 0.01249 (7) | −0.02360 (7) | 0.12746 (5) | 0.01488 (12) | |
H8 | 0.0624 | −0.0745 | 0.0904 | 0.018* | |
C9 | −0.03816 (7) | 0.09320 (7) | 0.08314 (4) | 0.01445 (11) | |
C10 | −0.16733 (8) | 0.11320 (8) | 0.06119 (5) | 0.01782 (13) | |
H10 | −0.2291 | 0.0543 | 0.0768 | 0.021* | |
C11 | −0.20688 (8) | 0.21942 (8) | 0.01633 (5) | 0.02000 (14) | |
H11 | −0.2949 | 0.2339 | 0.0018 | 0.024* | |
C12 | −0.11478 (8) | 0.30233 (8) | −0.00616 (5) | 0.01877 (14) | |
C13 | 0.01408 (8) | 0.28695 (7) | 0.01541 (5) | 0.01794 (13) | |
H13 | 0.0752 | 0.3466 | −0.0001 | 0.022* | |
C14 | 0.05168 (7) | 0.18179 (7) | 0.06049 (5) | 0.01634 (12) | |
H14 | 0.1397 | 0.1698 | 0.0762 | 0.020* | |
C15 | 0.45021 (7) | 0.19042 (7) | 0.11893 (4) | 0.01537 (12) | |
C16 | 0.42730 (8) | 0.30893 (8) | 0.15130 (5) | 0.01834 (13) | |
H16 | 0.4441 | 0.3238 | 0.2067 | 0.022* | |
C17 | 0.37957 (8) | 0.40491 (8) | 0.10122 (5) | 0.02021 (14) | |
H17 | 0.3638 | 0.4859 | 0.1224 | 0.024* | |
C18 | 0.35492 (9) | 0.38225 (8) | 0.01986 (5) | 0.02059 (14) | |
H18 | 0.3237 | 0.4484 | −0.0142 | 0.025* | |
C19 | 0.37574 (9) | 0.26312 (9) | −0.01171 (5) | 0.02074 (14) | |
H19 | 0.3576 | 0.2479 | −0.0670 | 0.025* | |
C20 | 0.42315 (8) | 0.16653 (8) | 0.03796 (5) | 0.01832 (13) | |
H20 | 0.4370 | 0.0850 | 0.0169 | 0.022* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.01822 (9) | 0.01926 (9) | 0.03139 (11) | −0.00416 (6) | 0.00132 (8) | 0.00568 (7) |
S2 | 0.01232 (8) | 0.01876 (8) | 0.01540 (8) | 0.00140 (5) | −0.00023 (6) | −0.00015 (6) |
F1 | 0.0321 (3) | 0.0217 (2) | 0.0303 (3) | 0.0092 (2) | −0.0023 (2) | 0.0074 (2) |
O1 | 0.0177 (3) | 0.0273 (3) | 0.0200 (3) | −0.0025 (2) | −0.0057 (2) | 0.0001 (2) |
O2 | 0.0173 (3) | 0.0234 (3) | 0.0226 (3) | 0.0061 (2) | 0.0041 (2) | −0.0012 (2) |
N1 | 0.0149 (3) | 0.0184 (3) | 0.0146 (3) | 0.0000 (2) | 0.0012 (2) | −0.0014 (2) |
N2 | 0.0139 (2) | 0.0150 (2) | 0.0134 (2) | 0.00161 (18) | 0.00123 (19) | 0.00065 (19) |
C1 | 0.0179 (3) | 0.0225 (3) | 0.0141 (3) | 0.0004 (2) | 0.0016 (2) | −0.0017 (2) |
C2 | 0.0194 (3) | 0.0232 (3) | 0.0153 (3) | 0.0014 (3) | 0.0006 (2) | 0.0057 (3) |
C3 | 0.0161 (3) | 0.0143 (3) | 0.0186 (3) | 0.0012 (2) | 0.0007 (2) | 0.0032 (2) |
C4 | 0.0155 (3) | 0.0163 (3) | 0.0191 (3) | 0.0008 (2) | 0.0002 (2) | −0.0025 (2) |
C5 | 0.0220 (4) | 0.0341 (4) | 0.0148 (3) | 0.0016 (3) | 0.0043 (3) | 0.0046 (3) |
C6 | 0.0202 (3) | 0.0233 (3) | 0.0157 (3) | 0.0055 (3) | 0.0040 (3) | 0.0006 (3) |
C7A | 0.0147 (14) | 0.043 (2) | 0.0204 (12) | −0.0080 (12) | 0.0035 (9) | 0.0017 (10) |
C7B | 0.0109 (10) | 0.107 (4) | 0.0210 (11) | −0.0014 (16) | 0.0023 (8) | 0.0010 (17) |
C8 | 0.0136 (3) | 0.0151 (3) | 0.0159 (3) | −0.0001 (2) | 0.0010 (2) | 0.0000 (2) |
C9 | 0.0137 (3) | 0.0159 (3) | 0.0137 (3) | 0.0011 (2) | 0.0012 (2) | −0.0007 (2) |
C10 | 0.0140 (3) | 0.0206 (3) | 0.0188 (3) | 0.0017 (2) | 0.0010 (2) | −0.0001 (3) |
C11 | 0.0159 (3) | 0.0228 (3) | 0.0210 (3) | 0.0058 (3) | −0.0008 (3) | −0.0003 (3) |
C12 | 0.0227 (4) | 0.0161 (3) | 0.0172 (3) | 0.0062 (2) | −0.0004 (3) | 0.0006 (2) |
C13 | 0.0207 (3) | 0.0161 (3) | 0.0171 (3) | 0.0009 (2) | 0.0013 (2) | 0.0016 (2) |
C14 | 0.0149 (3) | 0.0172 (3) | 0.0169 (3) | 0.0005 (2) | 0.0007 (2) | 0.0013 (2) |
C15 | 0.0137 (3) | 0.0177 (3) | 0.0147 (3) | 0.0000 (2) | 0.0005 (2) | −0.0003 (2) |
C16 | 0.0193 (3) | 0.0185 (3) | 0.0169 (3) | −0.0005 (2) | −0.0013 (2) | −0.0029 (2) |
C17 | 0.0218 (4) | 0.0175 (3) | 0.0210 (3) | 0.0008 (3) | −0.0007 (3) | −0.0014 (3) |
C18 | 0.0213 (4) | 0.0211 (3) | 0.0192 (3) | 0.0018 (3) | −0.0001 (3) | 0.0023 (3) |
C19 | 0.0236 (4) | 0.0236 (4) | 0.0149 (3) | 0.0033 (3) | 0.0006 (3) | 0.0001 (3) |
C20 | 0.0199 (3) | 0.0200 (3) | 0.0151 (3) | 0.0025 (2) | 0.0016 (2) | −0.0014 (2) |
Geometric parameters (Å, º) top
S1—C7A | 1.808 (3) | C6—H6B | 0.96 |
S1—C7B | 1.815 (3) | C7A—H7AA | 0.99 |
S1—C8 | 1.8445 (8) | C7A—H7AB | 0.99 |
S2—O2 | 1.4383 (7) | C7B—H7BA | 0.99 |
S2—O1 | 1.4386 (7) | C7B—H7BB | 0.99 |
S2—N1 | 1.6140 (7) | C8—C9 | 1.5224 (11) |
S2—C15 | 1.7669 (8) | C8—H8 | 1.00 |
F1—C12 | 1.3600 (10) | C9—C10 | 1.3941 (11) |
N1—C1 | 1.4732 (10) | C9—C14 | 1.4022 (11) |
N1—C4 | 1.4831 (10) | C10—C11 | 1.4026 (12) |
N2—C8 | 1.4477 (10) | C10—H10 | 0.95 |
N2—C3 | 1.4724 (10) | C11—C12 | 1.3786 (13) |
N2—C6 | 1.4780 (10) | C11—H11 | 0.95 |
C1—C2 | 1.5328 (12) | C12—C13 | 1.3831 (12) |
C1—H1A | 0.99 | C13—C14 | 1.3904 (11) |
C1—H1B | 0.99 | C13—H13 | 0.95 |
C2—C3 | 1.5368 (12) | C14—H14 | 0.95 |
C2—C5 | 1.5393 (12) | C15—C20 | 1.3949 (11) |
C2—H2 | 1.00 | C15—C16 | 1.3978 (11) |
C3—C4 | 1.5266 (11) | C16—C17 | 1.3920 (12) |
C3—H3 | 1.00 | C16—H16 | 0.95 |
C4—H4A | 0.99 | C17—C18 | 1.3959 (12) |
C4—H4B | 0.99 | C17—H17 | 0.95 |
C5—C6 | 1.5353 (12) | C18—C19 | 1.3943 (12) |
C5—H5A | 0.99 | C18—H18 | 0.95 |
C5—H5B | 0.99 | C19—C20 | 1.3917 (12) |
C6—C7B | 1.544 (3) | C19—H19 | 0.95 |
C6—C7A | 1.562 (3) | C20—H20 | 0.95 |
C6—H6A | 1.00 | | |
| | | |
C7A—S1—C8 | 92.77 (9) | C7A—C6—H6B | 123.6 |
C7B—S1—C8 | 90.22 (15) | C6—C7A—S1 | 107.23 (18) |
O2—S2—O1 | 120.42 (4) | C6—C7A—H7AA | 110.3 |
O2—S2—N1 | 106.05 (4) | S1—C7A—H7AA | 110.3 |
O1—S2—N1 | 107.00 (4) | C6—C7A—H7AB | 110.3 |
O2—S2—C15 | 107.05 (4) | S1—C7A—H7AB | 110.3 |
O1—S2—C15 | 107.46 (4) | H7AA—C7A—H7AB | 108.5 |
N1—S2—C15 | 108.42 (4) | C6—C7B—S1 | 107.67 (17) |
C1—N1—C4 | 111.81 (6) | C6—C7B—H7BA | 110.2 |
C1—N1—S2 | 121.77 (6) | S1—C7B—H7BA | 110.2 |
C4—N1—S2 | 119.94 (5) | C6—C7B—H7BB | 110.2 |
C8—N2—C3 | 115.24 (6) | S1—C7B—H7BB | 110.2 |
C8—N2—C6 | 109.26 (6) | H7BA—C7B—H7BB | 108.5 |
C3—N2—C6 | 106.97 (6) | N2—C8—C9 | 110.91 (6) |
N1—C1—C2 | 102.23 (6) | N2—C8—S1 | 106.21 (5) |
N1—C1—H1A | 111.3 | C9—C8—S1 | 114.69 (5) |
C2—C1—H1A | 111.3 | N2—C8—H8 | 108.3 |
N1—C1—H1B | 111.3 | C9—C8—H8 | 108.3 |
C2—C1—H1B | 111.3 | S1—C8—H8 | 108.3 |
H1A—C1—H1B | 109.2 | C10—C9—C14 | 118.96 (7) |
C1—C2—C3 | 102.36 (6) | C10—C9—C8 | 123.51 (7) |
C1—C2—C5 | 113.53 (7) | C14—C9—C8 | 117.47 (7) |
C3—C2—C5 | 105.02 (7) | C9—C10—C11 | 120.62 (8) |
C1—C2—H2 | 111.8 | C9—C10—H10 | 119.7 |
C3—C2—H2 | 111.8 | C11—C10—H10 | 119.7 |
C5—C2—H2 | 111.8 | C12—C11—C10 | 118.32 (7) |
N2—C3—C4 | 111.76 (6) | C12—C11—H11 | 120.8 |
N2—C3—C2 | 100.96 (6) | C10—C11—H11 | 120.8 |
C4—C3—C2 | 106.33 (6) | F1—C12—C11 | 118.91 (7) |
N2—C3—H3 | 112.4 | F1—C12—C13 | 118.25 (8) |
C4—C3—H3 | 112.4 | C11—C12—C13 | 122.84 (7) |
C2—C3—H3 | 112.4 | C12—C13—C14 | 118.14 (7) |
N1—C4—C3 | 103.32 (6) | C12—C13—H13 | 120.9 |
N1—C4—H4A | 111.1 | C14—C13—H13 | 120.9 |
C3—C4—H4A | 111.1 | C13—C14—C9 | 121.09 (7) |
N1—C4—H4B | 111.1 | C13—C14—H14 | 119.5 |
C3—C4—H4B | 111.1 | C9—C14—H14 | 119.5 |
H4A—C4—H4B | 109.1 | C20—C15—C16 | 121.01 (7) |
C6—C5—C2 | 104.83 (7) | C20—C15—S2 | 119.45 (6) |
C6—C5—H5A | 110.8 | C16—C15—S2 | 119.54 (6) |
C2—C5—H5A | 110.8 | C17—C16—C15 | 119.12 (7) |
C6—C5—H5B | 110.8 | C17—C16—H16 | 120.4 |
C2—C5—H5B | 110.8 | C15—C16—H16 | 120.4 |
H5A—C5—H5B | 108.9 | C16—C17—C18 | 120.08 (8) |
N2—C6—C5 | 104.98 (6) | C16—C17—H17 | 120.0 |
N2—C6—C7B | 110.82 (12) | C18—C17—H17 | 120.0 |
C5—C6—C7B | 119.3 (3) | C19—C18—C17 | 120.44 (8) |
N2—C6—C7A | 108.26 (16) | C19—C18—H18 | 119.8 |
C5—C6—C7A | 109.1 (2) | C17—C18—H18 | 119.8 |
N2—C6—H6A | 111.4 | C20—C19—C18 | 119.85 (8) |
C5—C6—H6A | 111.4 | C20—C19—H19 | 120.1 |
C7A—C6—H6A | 111.4 | C18—C19—H19 | 120.1 |
N2—C6—H6B | 104.7 | C19—C20—C15 | 119.47 (7) |
C5—C6—H6B | 104.8 | C19—C20—H20 | 120.3 |
C7B—C6—H6B | 111.1 | C15—C20—H20 | 120.3 |
| | | |
O2—S2—N1—C1 | 169.27 (6) | C7A—C6—C7B—S1 | −81.7 (8) |
O1—S2—N1—C1 | 39.57 (7) | C7A—S1—C7B—C6 | 83.9 (8) |
C15—S2—N1—C1 | −76.06 (7) | C8—S1—C7B—C6 | −19.2 (5) |
O2—S2—N1—C4 | −41.29 (7) | C3—N2—C8—C9 | −155.78 (6) |
O1—S2—N1—C4 | −171.00 (6) | C6—N2—C8—C9 | 83.80 (7) |
C15—S2—N1—C4 | 73.38 (7) | C3—N2—C8—S1 | 79.00 (7) |
C4—N1—C1—C2 | 27.87 (8) | C6—N2—C8—S1 | −41.42 (7) |
S2—N1—C1—C2 | 179.54 (5) | C7A—S1—C8—N2 | 24.2 (2) |
N1—C1—C2—C3 | −36.40 (8) | C7B—S1—C8—N2 | 35.2 (3) |
N1—C1—C2—C5 | −149.04 (7) | C7A—S1—C8—C9 | −98.7 (2) |
C8—N2—C3—C4 | 83.45 (8) | C7B—S1—C8—C9 | −87.7 (3) |
C6—N2—C3—C4 | −154.88 (7) | N2—C8—C9—C10 | −130.23 (8) |
C8—N2—C3—C2 | −163.87 (6) | S1—C8—C9—C10 | −9.93 (10) |
C6—N2—C3—C2 | −42.20 (8) | N2—C8—C9—C14 | 52.71 (9) |
C1—C2—C3—N2 | −83.23 (7) | S1—C8—C9—C14 | 173.01 (6) |
C5—C2—C3—N2 | 35.59 (8) | C14—C9—C10—C11 | 0.77 (12) |
C1—C2—C3—C4 | 33.52 (8) | C8—C9—C10—C11 | −176.25 (7) |
C5—C2—C3—C4 | 152.34 (7) | C9—C10—C11—C12 | 0.75 (12) |
C1—N1—C4—C3 | −7.07 (8) | C10—C11—C12—F1 | 178.86 (7) |
S2—N1—C4—C3 | −159.32 (5) | C10—C11—C12—C13 | −1.79 (13) |
N2—C3—C4—N1 | 92.37 (7) | F1—C12—C13—C14 | −179.42 (7) |
C2—C3—C4—N1 | −16.91 (8) | C11—C12—C13—C14 | 1.22 (13) |
C1—C2—C5—C6 | 94.12 (9) | C12—C13—C14—C9 | 0.39 (12) |
C3—C2—C5—C6 | −16.90 (9) | C10—C9—C14—C13 | −1.35 (12) |
C8—N2—C6—C5 | 157.55 (7) | C8—C9—C14—C13 | 175.84 (7) |
C3—N2—C6—C5 | 32.19 (9) | O2—S2—C15—C20 | 18.71 (8) |
C8—N2—C6—C7B | 27.5 (4) | O1—S2—C15—C20 | 149.37 (7) |
C3—N2—C6—C7B | −97.9 (4) | N1—S2—C15—C20 | −95.30 (7) |
C8—N2—C6—C7A | 41.2 (3) | O2—S2—C15—C16 | −161.48 (7) |
C3—N2—C6—C7A | −84.2 (3) | O1—S2—C15—C16 | −30.81 (8) |
C2—C5—C6—N2 | −8.31 (9) | N1—S2—C15—C16 | 84.52 (7) |
C2—C5—C6—C7B | 116.6 (3) | C20—C15—C16—C17 | −1.53 (12) |
C2—C5—C6—C7A | 107.5 (2) | S2—C15—C16—C17 | 178.66 (6) |
N2—C6—C7A—S1 | −21.2 (4) | C15—C16—C17—C18 | 0.14 (13) |
C5—C6—C7A—S1 | −134.9 (3) | C16—C17—C18—C19 | 1.09 (13) |
C7B—C6—C7A—S1 | 82.3 (8) | C17—C18—C19—C20 | −0.93 (14) |
C7B—S1—C7A—C6 | −78.7 (8) | C18—C19—C20—C15 | −0.45 (13) |
C8—S1—C7A—C6 | −1.5 (4) | C16—C15—C20—C19 | 1.69 (12) |
N2—C6—C7B—S1 | −0.6 (6) | S2—C15—C20—C19 | −178.50 (7) |
C5—C6—C7B—S1 | −122.6 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7B—H7BA···O1i | 0.99 | 2.59 | 3.558 (6) | 165 |
C10—H10···S1 | 0.95 | 2.67 | 3.1147 (9) | 109 |
C10—H10···O2i | 0.95 | 2.54 | 3.4353 (11) | 158 |
C20—H20···O2 | 0.95 | 2.55 | 2.9095 (11) | 103 |
C20—H20···O2ii | 0.95 | 2.57 | 3.2247 (11) | 127 |
C8—H8···Cg1iii | 1.00 | 2.55 | 3.4629 (9) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z; (iii) −x, −y, −z. |