The crystal structures of two benzothiophene derivatives are described and the intermolecular contacts in the crystals analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.
Supporting information
CCDC references: 2280606; 2280605
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 297 K
- Mean
![[sigma]](https://journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.042
- wR factor = 0.115
- Data-to-parameter ratio = 13.2
Structure: II
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.008 Å
- R factor = 0.066
- wR factor = 0.232
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT234_ALERT_4_C Large Hirshfeld Difference C1 --C7' . 0.18 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X H1N ..H10 . 1.98 Ang.
x,y,z = 1_555 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.048 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 9 Report
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 11 Note
PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum Found in CIF ...... Please Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 6 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for S1 --C1 . 5.5 s.u.
PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 11% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 11 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL 2019/3 Note
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL 2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 12 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 6 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
12 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Datablock: II
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.12
Rint given 0.155
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low .. 49% Check
PLAT048_ALERT_1_C MoietyFormula Not Given (or Incomplete) ........ Please Check
PLAT230_ALERT_2_C Hirshfeld Test Diff for S2 --O1 . 7.0 s.u.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00762 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -13.956 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -1.352 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 7 Report
Alert level G
PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum Found in CIF ...... Please Check
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 ......... 0.155 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H18 ..S1 . 3.01 Ang.
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL 2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 18 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
8 ALERT level G = General information/check it is not something unexpected
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
8 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
For both structures, data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS2018/3 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2020).
(
E)-
N-{2-[2-(Benzo[
b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide (I)
top
Crystal data top
| C22H16FNO2S2 | F(000) = 848 |
| Mr = 409.48 | Dx = 1.392 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 7.9588 (1) Å | Cell parameters from 9457 reflections |
| b = 25.9840 (4) Å | θ = 3.4–68.6° |
| c = 9.5178 (2) Å | µ = 2.70 mm−1 |
| β = 96.853 (1)° | T = 297 K |
| V = 1954.23 (6) Å3 | Block, brown |
| Z = 4 | 0.15 × 0.10 × 0.08 mm |
Data collection top
| Bruker D8 Venture Diffractometer | 2964 reflections with I > 2σ(I) |
| Radiation source: micro focus sealed tube | Rint = 0.049 |
| ω and φ scans | θmax = 68.7°, θmin = 3.4° |
Absorption correction: multi-scan
(SADABS; Bruker, 2016) | h = −9→9 |
| Tmin = 0.589, Tmax = 0.753 | k = −31→31 |
| 44325 measured reflections | l = −11→11 |
| 3597 independent reflections | |
Refinement top
| Refinement on F2 | 11 restraints |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0496P)2 + 0.7846P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 3597 reflections | Δρmax = 0.21 e Å−3 |
| 272 parameters | Δρmin = −0.28 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | Occ. (<1) |
| C1 | 0.7141 (2) | 0.64416 (6) | 0.53276 (16) | 0.0782 (7) | |
| C2 | 0.6743 (3) | 0.69557 (7) | 0.5055 (2) | 0.1055 (10) | |
| H2 | 0.611424 | 0.704923 | 0.420704 | 0.127* | |
| C3 | 0.7286 (3) | 0.73300 (5) | 0.6050 (3) | 0.1127 (11) | |
| H3 | 0.701996 | 0.767393 | 0.586823 | 0.135* | |
| C4 | 0.8226 (3) | 0.71902 (7) | 0.7318 (2) | 0.1109 (11) | |
| H4 | 0.858902 | 0.744059 | 0.798407 | 0.133* | |
| C5 | 0.8623 (3) | 0.66761 (8) | 0.75906 (17) | 0.1018 (9) | |
| H5 | 0.925238 | 0.658254 | 0.843872 | 0.122* | |
| C6 | 0.8081 (2) | 0.63018 (5) | 0.65953 (18) | 0.0788 (7) | |
| S1' | 0.8669 (7) | 0.56832 (19) | 0.7105 (5) | 0.0855 (14) | 0.243 (4) |
| C7' | 0.709 (3) | 0.5902 (6) | 0.4679 (19) | 0.103 (8) | 0.243 (4) |
| H7' | 0.649984 | 0.584659 | 0.378833 | 0.124* | 0.243 (4) |
| C8' | 0.790 (5) | 0.5504 (7) | 0.539 (2) | 0.051 (5) | 0.243 (4) |
| S1 | 0.6512 (2) | 0.59509 (5) | 0.41950 (14) | 0.0758 (4) | 0.757 (4) |
| C7 | 0.8282 (9) | 0.5758 (2) | 0.6526 (7) | 0.0900 (18) | 0.757 (4) |
| H7 | 0.893320 | 0.557894 | 0.724278 | 0.108* | 0.757 (4) |
| C8 | 0.7498 (15) | 0.5511 (3) | 0.5389 (9) | 0.067 (3) | 0.757 (4) |
| C9 | 0.7644 (3) | 0.49638 (9) | 0.5064 (3) | 0.0754 (6) | |
| H9 | 0.808242 | 0.474482 | 0.579001 | 0.090* | |
| C10 | 0.6922 (3) | 0.47259 (9) | 0.3953 (3) | 0.0741 (6) | |
| H10 | 0.632873 | 0.492988 | 0.325994 | 0.089* | |
| C11 | 0.6936 (3) | 0.41711 (8) | 0.3671 (2) | 0.0673 (6) | |
| C12 | 0.7752 (4) | 0.38326 (10) | 0.4678 (3) | 0.0976 (9) | |
| H12 | 0.829122 | 0.396833 | 0.551708 | 0.117* | |
| C13 | 0.7790 (5) | 0.33108 (10) | 0.4481 (3) | 0.1019 (10) | |
| H13 | 0.835045 | 0.309475 | 0.516146 | 0.122* | |
| C14 | 0.6980 (4) | 0.31212 (9) | 0.3256 (3) | 0.0837 (7) | |
| C15 | 0.6143 (3) | 0.34215 (8) | 0.2231 (3) | 0.0711 (6) | |
| H15 | 0.557999 | 0.327509 | 0.141557 | 0.085* | |
| C16 | 0.6145 (3) | 0.39533 (7) | 0.2428 (2) | 0.0578 (5) | |
| C17 | 0.6983 (2) | 0.40434 (7) | −0.0853 (2) | 0.0545 (5) | |
| C18 | 0.8053 (3) | 0.44596 (9) | −0.0912 (3) | 0.0739 (6) | |
| H18 | 0.770751 | 0.478886 | −0.069161 | 0.089* | |
| C19 | 0.9636 (3) | 0.43766 (13) | −0.1303 (3) | 0.0927 (8) | |
| H19 | 1.037422 | 0.465199 | −0.134587 | 0.111* | |
| C20 | 1.0139 (3) | 0.38892 (15) | −0.1632 (3) | 0.0947 (9) | |
| H20 | 1.121259 | 0.383777 | −0.189882 | 0.114* | |
| C21 | 0.9072 (4) | 0.34806 (12) | −0.1569 (3) | 0.0888 (8) | |
| H21 | 0.942294 | 0.315210 | −0.179119 | 0.107* | |
| C22 | 0.7481 (3) | 0.35538 (9) | −0.1179 (2) | 0.0689 (6) | |
| H22 | 0.675016 | 0.327657 | −0.113642 | 0.083* | |
| N1 | 0.5283 (2) | 0.42741 (6) | 0.1368 (2) | 0.0616 (4) | |
| O1 | 0.40697 (18) | 0.36642 (5) | −0.05058 (18) | 0.0706 (4) | |
| O2 | 0.42235 (19) | 0.45927 (5) | −0.09632 (17) | 0.0674 (4) | |
| F1 | 0.6977 (3) | 0.26050 (5) | 0.3036 (2) | 0.1171 (6) | |
| S2 | 0.49738 (6) | 0.41360 (2) | −0.03136 (6) | 0.05557 (17) | |
| H1N | 0.545 (3) | 0.4587 (6) | 0.147 (2) | 0.067* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.0989 (18) | 0.0723 (15) | 0.0687 (14) | −0.0213 (13) | 0.0318 (13) | −0.0024 (12) |
| C2 | 0.132 (3) | 0.0839 (19) | 0.103 (2) | −0.0145 (18) | 0.0231 (19) | 0.0204 (17) |
| C3 | 0.135 (3) | 0.0621 (16) | 0.149 (3) | −0.0154 (17) | 0.052 (3) | −0.0014 (19) |
| C4 | 0.135 (3) | 0.081 (2) | 0.126 (3) | −0.0312 (19) | 0.054 (2) | −0.0337 (19) |
| C5 | 0.124 (2) | 0.099 (2) | 0.0829 (18) | −0.0240 (19) | 0.0139 (17) | −0.0201 (16) |
| C6 | 0.0929 (17) | 0.0706 (15) | 0.0766 (16) | −0.0123 (13) | 0.0252 (13) | −0.0080 (12) |
| S1' | 0.104 (3) | 0.077 (2) | 0.074 (3) | −0.0128 (19) | 0.004 (2) | −0.0059 (19) |
| C7' | 0.127 (16) | 0.121 (16) | 0.059 (10) | −0.069 (13) | 0.001 (8) | −0.016 (10) |
| C8' | 0.045 (12) | 0.060 (8) | 0.050 (8) | −0.004 (5) | 0.017 (5) | 0.001 (6) |
| S1 | 0.1095 (10) | 0.0607 (5) | 0.0576 (8) | −0.0079 (5) | 0.0109 (6) | −0.0006 (4) |
| C7 | 0.111 (4) | 0.077 (3) | 0.076 (4) | 0.003 (2) | −0.010 (3) | 0.000 (3) |
| C8 | 0.065 (6) | 0.067 (3) | 0.071 (3) | −0.009 (2) | 0.017 (2) | −0.003 (2) |
| C9 | 0.0896 (17) | 0.0647 (14) | 0.0712 (14) | 0.0018 (12) | 0.0068 (12) | 0.0001 (11) |
| C10 | 0.1028 (18) | 0.0551 (12) | 0.0632 (13) | −0.0022 (12) | 0.0055 (12) | 0.0060 (10) |
| C11 | 0.0864 (15) | 0.0516 (11) | 0.0647 (13) | 0.0000 (10) | 0.0123 (11) | 0.0086 (10) |
| C12 | 0.142 (3) | 0.0674 (16) | 0.0772 (17) | −0.0011 (16) | −0.0111 (17) | 0.0139 (13) |
| C13 | 0.141 (3) | 0.0651 (16) | 0.095 (2) | 0.0093 (16) | −0.0046 (19) | 0.0296 (15) |
| C14 | 0.114 (2) | 0.0459 (12) | 0.0930 (19) | 0.0051 (12) | 0.0186 (16) | 0.0146 (12) |
| C15 | 0.0888 (16) | 0.0472 (11) | 0.0783 (15) | 0.0022 (11) | 0.0142 (12) | 0.0065 (10) |
| C16 | 0.0645 (12) | 0.0457 (10) | 0.0658 (12) | 0.0025 (9) | 0.0186 (10) | 0.0083 (9) |
| C17 | 0.0545 (10) | 0.0502 (10) | 0.0561 (11) | −0.0008 (8) | −0.0041 (8) | −0.0033 (8) |
| C18 | 0.0654 (13) | 0.0673 (14) | 0.0871 (16) | −0.0139 (11) | 0.0014 (12) | −0.0091 (12) |
| C19 | 0.0671 (15) | 0.116 (2) | 0.0935 (19) | −0.0253 (16) | 0.0020 (14) | −0.0039 (17) |
| C20 | 0.0562 (14) | 0.147 (3) | 0.0796 (17) | 0.0120 (17) | 0.0026 (12) | −0.0036 (18) |
| C21 | 0.0794 (17) | 0.096 (2) | 0.0904 (19) | 0.0269 (15) | 0.0098 (14) | −0.0087 (15) |
| C22 | 0.0724 (14) | 0.0582 (12) | 0.0752 (14) | 0.0077 (10) | 0.0049 (11) | −0.0050 (11) |
| N1 | 0.0745 (11) | 0.0401 (8) | 0.0700 (11) | 0.0070 (8) | 0.0081 (9) | 0.0009 (8) |
| O1 | 0.0613 (8) | 0.0459 (7) | 0.1008 (12) | −0.0087 (6) | −0.0061 (8) | −0.0028 (7) |
| O2 | 0.0711 (9) | 0.0437 (7) | 0.0826 (10) | 0.0098 (6) | −0.0111 (7) | 0.0015 (7) |
| F1 | 0.1731 (17) | 0.0454 (8) | 0.1300 (14) | 0.0126 (9) | 0.0067 (12) | 0.0189 (8) |
| S2 | 0.0546 (3) | 0.0379 (2) | 0.0718 (3) | 0.00112 (18) | −0.0029 (2) | −0.0018 (2) |
Geometric parameters (Å, º) top
| C1—C2 | 1.3900 | C11—C12 | 1.402 (3) |
| C1—C6 | 1.3900 | C12—C13 | 1.369 (4) |
| C1—C7' | 1.531 (14) | C12—H12 | 0.9300 |
| C1—S1 | 1.7058 (18) | C13—C14 | 1.356 (4) |
| C2—C3 | 1.3900 | C13—H13 | 0.9300 |
| C2—H2 | 0.9300 | C14—F1 | 1.358 (3) |
| C3—C4 | 1.3900 | C14—C15 | 1.360 (3) |
| C3—H3 | 0.9300 | C15—C16 | 1.394 (3) |
| C4—C5 | 1.3900 | C15—H15 | 0.9300 |
| C4—H4 | 0.9300 | C16—N1 | 1.421 (3) |
| C5—C6 | 1.3900 | C17—C22 | 1.379 (3) |
| C5—H5 | 0.9300 | C17—C18 | 1.381 (3) |
| C6—C7 | 1.426 (6) | C17—S2 | 1.754 (2) |
| C6—S1' | 1.727 (5) | C18—C19 | 1.373 (4) |
| S1'—C8' | 1.738 (17) | C18—H18 | 0.9300 |
| C7'—C8' | 1.356 (18) | C19—C20 | 1.375 (4) |
| C7'—H7' | 0.9300 | C19—H19 | 0.9300 |
| C8'—C9 | 1.446 (17) | C20—C21 | 1.365 (4) |
| S1—C8 | 1.732 (7) | C20—H20 | 0.9300 |
| C7—C8 | 1.345 (8) | C21—C22 | 1.375 (4) |
| C7—H7 | 0.9300 | C21—H21 | 0.9300 |
| C8—C9 | 1.463 (7) | C22—H22 | 0.9300 |
| C9—C10 | 1.298 (3) | N1—S2 | 1.6301 (19) |
| C9—H9 | 0.9300 | N1—H1N | 0.828 (16) |
| C10—C11 | 1.467 (3) | O1—S2 | 1.4222 (14) |
| C10—H10 | 0.9300 | O2—S2 | 1.4348 (14) |
| C11—C16 | 1.393 (3) | | |
| | | |
| C2—C1—C6 | 120.0 | C16—C11—C10 | 122.8 (2) |
| C2—C1—C7' | 144.2 (7) | C12—C11—C10 | 120.3 (2) |
| C6—C1—C7' | 95.5 (7) | C13—C12—C11 | 122.9 (3) |
| C2—C1—S1 | 123.88 (12) | C13—C12—H12 | 118.5 |
| C6—C1—S1 | 116.11 (12) | C11—C12—H12 | 118.5 |
| C3—C2—C1 | 120.0 | C14—C13—C12 | 117.5 (3) |
| C3—C2—H2 | 120.0 | C14—C13—H13 | 121.3 |
| C1—C2—H2 | 120.0 | C12—C13—H13 | 121.3 |
| C2—C3—C4 | 120.0 | C13—C14—F1 | 118.9 (2) |
| C2—C3—H3 | 120.0 | C13—C14—C15 | 123.4 (2) |
| C4—C3—H3 | 120.0 | F1—C14—C15 | 117.7 (3) |
| C5—C4—C3 | 120.0 | C14—C15—C16 | 118.6 (2) |
| C5—C4—H4 | 120.0 | C14—C15—H15 | 120.7 |
| C3—C4—H4 | 120.0 | C16—C15—H15 | 120.7 |
| C4—C5—C6 | 120.0 | C11—C16—C15 | 120.7 (2) |
| C4—C5—H5 | 120.0 | C11—C16—N1 | 119.74 (18) |
| C6—C5—H5 | 120.0 | C15—C16—N1 | 119.6 (2) |
| C5—C6—C1 | 120.0 | C22—C17—C18 | 121.2 (2) |
| C5—C6—C7 | 134.3 (3) | C22—C17—S2 | 119.30 (17) |
| C1—C6—C7 | 105.7 (3) | C18—C17—S2 | 119.49 (17) |
| C5—C6—S1' | 114.1 (2) | C19—C18—C17 | 118.5 (2) |
| C1—C6—S1' | 125.9 (2) | C19—C18—H18 | 120.7 |
| C6—S1'—C8' | 86.1 (6) | C17—C18—H18 | 120.7 |
| C8'—C7'—C1 | 120.6 (13) | C18—C19—C20 | 120.5 (3) |
| C8'—C7'—H7' | 119.7 | C18—C19—H19 | 119.7 |
| C1—C7'—H7' | 119.7 | C20—C19—H19 | 119.7 |
| C7'—C8'—C9 | 126.0 (15) | C21—C20—C19 | 120.5 (3) |
| C7'—C8'—S1' | 110.9 (13) | C21—C20—H20 | 119.8 |
| C9—C8'—S1' | 119.1 (13) | C19—C20—H20 | 119.8 |
| C1—S1—C8 | 90.1 (2) | C20—C21—C22 | 120.1 (3) |
| C8—C7—C6 | 117.7 (6) | C20—C21—H21 | 119.9 |
| C8—C7—H7 | 121.1 | C22—C21—H21 | 119.9 |
| C6—C7—H7 | 121.1 | C21—C22—C17 | 119.2 (2) |
| C7—C8—C9 | 126.3 (6) | C21—C22—H22 | 120.4 |
| C7—C8—S1 | 110.1 (5) | C17—C22—H22 | 120.4 |
| C9—C8—S1 | 122.9 (5) | C16—N1—S2 | 124.85 (14) |
| C10—C9—C8' | 132.4 (8) | C16—N1—H1N | 116.0 (16) |
| C10—C9—C8 | 126.6 (4) | S2—N1—H1N | 109.5 (16) |
| C10—C9—H9 | 113.8 | O1—S2—O2 | 118.64 (9) |
| C8'—C9—H9 | 113.8 | O1—S2—N1 | 109.32 (10) |
| C9—C10—C11 | 127.2 (2) | O2—S2—N1 | 104.32 (9) |
| C9—C10—H10 | 116.4 | O1—S2—C17 | 108.01 (9) |
| C11—C10—H10 | 116.4 | O2—S2—C17 | 109.55 (10) |
| C16—C11—C12 | 116.8 (2) | N1—S2—C17 | 106.35 (9) |
| | | |
| C6—C1—C2—C3 | 0.0 | C8'—C9—C10—C11 | 171 (2) |
| C7'—C1—C2—C3 | −171.5 (14) | C8—C9—C10—C11 | −174.3 (7) |
| S1—C1—C2—C3 | 178.91 (16) | C9—C10—C11—C16 | −178.7 (3) |
| C1—C2—C3—C4 | 0.0 | C9—C10—C11—C12 | 2.1 (4) |
| C2—C3—C4—C5 | 0.0 | C16—C11—C12—C13 | −0.1 (5) |
| C3—C4—C5—C6 | 0.0 | C10—C11—C12—C13 | 179.2 (3) |
| C4—C5—C6—C1 | 0.0 | C11—C12—C13—C14 | −0.7 (5) |
| C4—C5—C6—C7 | 178.8 (4) | C12—C13—C14—F1 | −179.2 (3) |
| C4—C5—C6—S1' | −179.6 (2) | C12—C13—C14—C15 | −0.1 (5) |
| C2—C1—C6—C5 | 0.0 | C13—C14—C15—C16 | 1.5 (4) |
| C7'—C1—C6—C5 | 175.0 (8) | F1—C14—C15—C16 | −179.3 (2) |
| S1—C1—C6—C5 | −178.99 (15) | C12—C11—C16—C15 | 1.6 (4) |
| C2—C1—C6—C7 | −179.1 (3) | C10—C11—C16—C15 | −177.7 (2) |
| S1—C1—C6—C7 | 1.9 (3) | C12—C11—C16—N1 | 179.5 (2) |
| C2—C1—C6—S1' | 179.5 (3) | C10—C11—C16—N1 | 0.2 (3) |
| C7'—C1—C6—S1' | −5.5 (8) | C14—C15—C16—C11 | −2.3 (4) |
| C5—C6—S1'—C8' | −171.8 (13) | C14—C15—C16—N1 | 179.8 (2) |
| C1—C6—S1'—C8' | 8.7 (14) | C22—C17—C18—C19 | −0.1 (4) |
| C2—C1—C7'—C8' | 171 (2) | S2—C17—C18—C19 | 178.41 (19) |
| C6—C1—C7'—C8' | −2 (3) | C17—C18—C19—C20 | 0.2 (4) |
| C1—C7'—C8'—C9 | 165 (2) | C18—C19—C20—C21 | −0.2 (4) |
| C1—C7'—C8'—S1' | 8 (4) | C19—C20—C21—C22 | 0.2 (4) |
| C6—S1'—C8'—C7' | −8 (2) | C20—C21—C22—C17 | −0.1 (4) |
| C6—S1'—C8'—C9 | −167 (3) | C18—C17—C22—C21 | 0.0 (4) |
| C2—C1—S1—C8 | −178.8 (5) | S2—C17—C22—C21 | −178.48 (19) |
| C6—C1—S1—C8 | 0.1 (5) | C11—C16—N1—S2 | 153.99 (18) |
| C5—C6—C7—C8 | 177.3 (7) | C15—C16—N1—S2 | −28.1 (3) |
| C1—C6—C7—C8 | −3.8 (9) | C16—N1—S2—O1 | 58.1 (2) |
| C6—C7—C8—C9 | 175.1 (8) | C16—N1—S2—O2 | −174.05 (17) |
| C6—C7—C8—S1 | 4.0 (11) | C16—N1—S2—C17 | −58.28 (19) |
| C1—S1—C8—C7 | −2.2 (8) | C22—C17—S2—O1 | −8.2 (2) |
| C1—S1—C8—C9 | −173.7 (9) | C18—C17—S2—O1 | 173.24 (18) |
| C7'—C8'—C9—C10 | 15 (5) | C22—C17—S2—O2 | −138.77 (17) |
| S1'—C8'—C9—C10 | 170.8 (10) | C18—C17—S2—O2 | 42.7 (2) |
| C7—C8—C9—C10 | −178.3 (8) | C22—C17—S2—N1 | 109.03 (18) |
| S1—C8—C9—C10 | −8.4 (13) | C18—C17—S2—N1 | −69.51 (19) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C15—H15···O1 | 0.93 | 2.30 | 2.980 (3) | 130 |
| C10—H10···02i | 0.93 | 2.51 | 3.383 (3) | 157 |
| N1—H1N···O2i | 0.83 (2) | 2.21 (2) | 3.001 (2) | 161 (2) |
| C22—H22···F1ii | 0.93 | 2.44 | 3.116 (3) | 130 |
| Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, −y+1/2, z−1/2. |
(
E)-
N-{2-[2-(Benzo[
b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-
N-(but-2-yn-1-yl)benzenesulfonamide (II)
top
Crystal data top
| C26H20FNO2S2 | F(000) = 960 |
| Mr = 461.55 | Dx = 1.327 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 9.3517 (3) Å | Cell parameters from 3616 reflections |
| b = 31.7075 (11) Å | θ = 2.8–65.4° |
| c = 8.6063 (3) Å | µ = 2.35 mm−1 |
| β = 115.179 (2)° | T = 297 K |
| V = 2309.45 (14) Å3 | Solid, white |
| Z = 4 | 0.11 × 0.07 × 0.02 mm |
Data collection top
| Bruker D8 Venture Diffractometer | 2098 reflections with I > 2σ(I) |
| Radiation source: micro focus sealed tube | Rint = 0.155 |
| ω and φ scans | θmax = 68.8°, θmin = 5.2° |
Absorption correction: multi-scan
(SADABS; Bruker, 2016) | h = −11→11 |
| Tmin = 0.604, Tmax = 0.753 | k = −37→38 |
| 39443 measured reflections | l = −10→10 |
| 4270 independent reflections | |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.066 | w = 1/[σ2(Fo2) + (0.1325P)2]
where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.232 | (Δ/σ)max < 0.001 |
| S = 1.00 | Δρmax = 0.33 e Å−3 |
| 4270 reflections | Δρmin = −0.37 e Å−3 |
| 291 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0040 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C1 | 0.2549 (6) | 0.32808 (15) | −0.0285 (6) | 0.0669 (12) | |
| C2 | 0.2360 (6) | 0.33934 (17) | −0.1918 (6) | 0.0778 (14) | |
| H2 | 0.311900 | 0.355578 | −0.207042 | 0.093* | |
| C3 | 0.1029 (7) | 0.32600 (17) | −0.3309 (7) | 0.0825 (15) | |
| H3 | 0.089065 | 0.333320 | −0.441041 | 0.099* | |
| C4 | −0.0110 (6) | 0.30184 (16) | −0.3096 (6) | 0.0763 (14) | |
| H4 | −0.100010 | 0.293249 | −0.405677 | 0.092* | |
| C5 | 0.0054 (6) | 0.29044 (15) | −0.1498 (6) | 0.0722 (13) | |
| H5 | −0.071951 | 0.274308 | −0.137015 | 0.087* | |
| C6 | 0.1408 (5) | 0.30337 (14) | −0.0042 (5) | 0.0626 (11) | |
| C7 | 0.1836 (6) | 0.29535 (14) | 0.1732 (6) | 0.0673 (12) | |
| H7 | 0.122120 | 0.279321 | 0.212083 | 0.081* | |
| C8 | 0.3227 (5) | 0.31338 (13) | 0.2798 (5) | 0.0609 (11) | |
| C9 | 0.3969 (6) | 0.31034 (15) | 0.4648 (6) | 0.0682 (12) | |
| H9 | 0.350312 | 0.292242 | 0.514847 | 0.082* | |
| C10 | 0.5265 (6) | 0.33107 (14) | 0.5712 (6) | 0.0633 (12) | |
| H10 | 0.571084 | 0.350331 | 0.523168 | 0.076* | |
| C11 | 0.6030 (5) | 0.32555 (13) | 0.7581 (5) | 0.0586 (11) | |
| C12 | 0.5852 (6) | 0.28800 (14) | 0.8336 (6) | 0.0659 (12) | |
| H12 | 0.521274 | 0.266825 | 0.763600 | 0.079* | |
| C13 | 0.6595 (6) | 0.28137 (15) | 1.0084 (6) | 0.0702 (13) | |
| H13 | 0.646816 | 0.256223 | 1.056735 | 0.084* | |
| C14 | 0.7527 (6) | 0.31322 (16) | 1.1085 (6) | 0.0718 (13) | |
| C15 | 0.7743 (6) | 0.35085 (15) | 1.0435 (6) | 0.0694 (13) | |
| H15 | 0.836300 | 0.371959 | 1.115842 | 0.083* | |
| C16 | 0.7016 (5) | 0.35672 (13) | 0.8677 (5) | 0.0585 (11) | |
| C17 | 0.6526 (6) | 0.45543 (14) | 0.9821 (6) | 0.0688 (13) | |
| C18 | 0.5818 (8) | 0.43930 (18) | 1.0789 (7) | 0.0899 (17) | |
| H18 | 0.505581 | 0.418355 | 1.033546 | 0.108* | |
| C19 | 0.6226 (9) | 0.4539 (2) | 1.2444 (9) | 0.106 (2) | |
| H19 | 0.574503 | 0.442786 | 1.310278 | 0.128* | |
| C20 | 0.7344 (9) | 0.4848 (2) | 1.3093 (9) | 0.109 (2) | |
| H20 | 0.762946 | 0.494415 | 1.420623 | 0.131* | |
| C21 | 0.8042 (9) | 0.5017 (2) | 1.2151 (9) | 0.109 (2) | |
| H21 | 0.878624 | 0.523052 | 1.260868 | 0.130* | |
| C22 | 0.7647 (7) | 0.48710 (16) | 1.0491 (7) | 0.0872 (16) | |
| H22 | 0.812980 | 0.498474 | 0.983836 | 0.105* | |
| C23 | 0.8877 (6) | 0.40504 (16) | 0.8143 (7) | 0.0763 (14) | |
| H23A | 0.925473 | 0.380835 | 0.773623 | 0.092* | |
| H23B | 0.882648 | 0.428675 | 0.740500 | 0.092* | |
| C24 | 1.0039 (6) | 0.41494 (15) | 0.9891 (7) | 0.0764 (14) | |
| C25 | 1.0953 (7) | 0.42202 (17) | 1.1328 (8) | 0.0886 (17) | |
| C26 | 1.2031 (8) | 0.4310 (2) | 1.3114 (8) | 0.117 (2) | |
| H26A | 1.143024 | 0.438114 | 1.374590 | 0.175* | |
| H26B | 1.270375 | 0.454214 | 1.315234 | 0.175* | |
| H26C | 1.266516 | 0.406545 | 1.361637 | 0.175* | |
| N1 | 0.7255 (4) | 0.39583 (10) | 0.7947 (5) | 0.0613 (10) | |
| O1 | 0.4505 (4) | 0.41733 (11) | 0.7156 (4) | 0.0851 (11) | |
| O2 | 0.6400 (5) | 0.46681 (11) | 0.6790 (5) | 0.0949 (12) | |
| S1 | 0.40923 (16) | 0.34048 (5) | 0.16627 (16) | 0.0776 (5) | |
| S2 | 0.60508 (16) | 0.43535 (4) | 0.77698 (15) | 0.0715 (4) | |
| F1 | 0.8245 (4) | 0.30760 (10) | 1.2817 (3) | 0.0982 (10) | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.060 (3) | 0.078 (3) | 0.063 (3) | −0.003 (2) | 0.026 (2) | −0.005 (2) |
| C2 | 0.073 (3) | 0.097 (4) | 0.066 (3) | −0.005 (3) | 0.033 (3) | 0.000 (3) |
| C3 | 0.080 (4) | 0.107 (4) | 0.059 (3) | 0.005 (3) | 0.029 (3) | −0.003 (3) |
| C4 | 0.074 (3) | 0.089 (3) | 0.062 (3) | 0.001 (3) | 0.025 (3) | −0.013 (2) |
| C5 | 0.063 (3) | 0.079 (3) | 0.066 (3) | −0.008 (2) | 0.019 (2) | −0.013 (2) |
| C6 | 0.060 (3) | 0.071 (3) | 0.056 (2) | −0.001 (2) | 0.024 (2) | −0.008 (2) |
| C7 | 0.065 (3) | 0.072 (3) | 0.065 (3) | −0.015 (2) | 0.028 (2) | −0.005 (2) |
| C8 | 0.063 (3) | 0.064 (2) | 0.057 (2) | −0.005 (2) | 0.027 (2) | −0.003 (2) |
| C9 | 0.068 (3) | 0.071 (3) | 0.061 (3) | −0.007 (2) | 0.023 (2) | −0.004 (2) |
| C10 | 0.064 (3) | 0.065 (3) | 0.059 (2) | −0.001 (2) | 0.025 (2) | 0.000 (2) |
| C11 | 0.057 (3) | 0.061 (2) | 0.057 (2) | 0.000 (2) | 0.024 (2) | 0.0004 (19) |
| C12 | 0.068 (3) | 0.064 (3) | 0.066 (3) | −0.003 (2) | 0.029 (2) | 0.000 (2) |
| C13 | 0.076 (3) | 0.070 (3) | 0.067 (3) | 0.000 (3) | 0.034 (3) | 0.007 (2) |
| C14 | 0.079 (3) | 0.081 (3) | 0.049 (2) | 0.007 (3) | 0.021 (2) | 0.009 (2) |
| C15 | 0.070 (3) | 0.070 (3) | 0.060 (3) | −0.001 (2) | 0.020 (2) | −0.001 (2) |
| C16 | 0.062 (3) | 0.056 (2) | 0.057 (2) | 0.002 (2) | 0.025 (2) | 0.0017 (18) |
| C17 | 0.076 (3) | 0.063 (3) | 0.070 (3) | 0.003 (2) | 0.033 (3) | −0.001 (2) |
| C18 | 0.107 (5) | 0.085 (3) | 0.081 (4) | −0.009 (3) | 0.044 (3) | −0.010 (3) |
| C19 | 0.132 (6) | 0.106 (4) | 0.096 (5) | 0.003 (4) | 0.063 (4) | −0.003 (4) |
| C20 | 0.134 (6) | 0.110 (5) | 0.079 (4) | 0.016 (5) | 0.042 (4) | −0.019 (4) |
| C21 | 0.119 (5) | 0.096 (4) | 0.099 (5) | −0.019 (4) | 0.034 (4) | −0.035 (4) |
| C22 | 0.099 (4) | 0.072 (3) | 0.088 (4) | −0.016 (3) | 0.038 (3) | −0.014 (3) |
| C23 | 0.074 (3) | 0.076 (3) | 0.081 (3) | −0.009 (3) | 0.035 (3) | −0.005 (2) |
| C24 | 0.068 (3) | 0.068 (3) | 0.090 (4) | −0.008 (3) | 0.031 (3) | −0.005 (3) |
| C25 | 0.081 (4) | 0.075 (3) | 0.101 (4) | −0.008 (3) | 0.030 (3) | −0.008 (3) |
| C26 | 0.102 (5) | 0.123 (5) | 0.093 (4) | −0.012 (4) | 0.010 (4) | −0.015 (4) |
| N1 | 0.064 (2) | 0.0555 (19) | 0.061 (2) | −0.0017 (17) | 0.0238 (18) | 0.0022 (16) |
| O1 | 0.062 (2) | 0.084 (2) | 0.088 (2) | 0.0006 (18) | 0.0117 (18) | −0.0075 (18) |
| O2 | 0.139 (3) | 0.0680 (19) | 0.077 (2) | 0.000 (2) | 0.045 (2) | 0.0174 (17) |
| S1 | 0.0655 (8) | 0.0998 (9) | 0.0656 (7) | −0.0180 (7) | 0.0261 (6) | −0.0056 (6) |
| S2 | 0.0822 (9) | 0.0616 (6) | 0.0625 (7) | 0.0020 (6) | 0.0229 (6) | 0.0030 (5) |
| F1 | 0.114 (2) | 0.107 (2) | 0.0552 (16) | −0.0063 (19) | 0.0187 (16) | 0.0166 (15) |
Geometric parameters (Å, º) top
| C1—C2 | 1.387 (7) | C15—C16 | 1.382 (6) |
| C1—C6 | 1.409 (7) | C15—H15 | 0.9300 |
| C1—S1 | 1.729 (5) | C16—N1 | 1.450 (5) |
| C2—C3 | 1.376 (7) | C17—C18 | 1.365 (7) |
| C2—H2 | 0.9300 | C17—C22 | 1.387 (7) |
| C3—C4 | 1.386 (7) | C17—S2 | 1.747 (5) |
| C3—H3 | 0.9300 | C18—C19 | 1.388 (8) |
| C4—C5 | 1.367 (7) | C18—H18 | 0.9300 |
| C4—H4 | 0.9300 | C19—C20 | 1.368 (9) |
| C5—C6 | 1.411 (6) | C19—H19 | 0.9300 |
| C5—H5 | 0.9300 | C20—C21 | 1.349 (9) |
| C6—C7 | 1.426 (6) | C20—H20 | 0.9300 |
| C7—C8 | 1.358 (6) | C21—C22 | 1.394 (8) |
| C7—H7 | 0.9300 | C21—H21 | 0.9300 |
| C8—C9 | 1.444 (6) | C22—H22 | 0.9300 |
| C8—S1 | 1.738 (5) | C23—C24 | 1.467 (7) |
| C9—C10 | 1.340 (6) | C23—N1 | 1.483 (6) |
| C9—H9 | 0.9300 | C23—H23A | 0.9700 |
| C10—C11 | 1.466 (6) | C23—H23B | 0.9700 |
| C10—H10 | 0.9300 | C24—C25 | 1.188 (7) |
| C11—C12 | 1.400 (6) | C25—C26 | 1.464 (8) |
| C11—C16 | 1.406 (6) | C26—H26A | 0.9600 |
| C12—C13 | 1.378 (6) | C26—H26B | 0.9600 |
| C12—H12 | 0.9300 | C26—H26C | 0.9600 |
| C13—C14 | 1.372 (7) | N1—S2 | 1.648 (4) |
| C13—H13 | 0.9300 | O1—S2 | 1.431 (4) |
| C14—F1 | 1.361 (5) | O2—S2 | 1.431 (4) |
| C14—C15 | 1.369 (7) | | |
| | | |
| C2—C1—C6 | 121.0 (4) | C15—C16—C11 | 121.1 (4) |
| C2—C1—S1 | 128.2 (4) | C15—C16—N1 | 119.7 (4) |
| C6—C1—S1 | 110.8 (3) | C11—C16—N1 | 119.2 (4) |
| C3—C2—C1 | 118.7 (5) | C18—C17—C22 | 119.6 (5) |
| C3—C2—H2 | 120.6 | C18—C17—S2 | 119.9 (4) |
| C1—C2—H2 | 120.6 | C22—C17—S2 | 120.4 (4) |
| C2—C3—C4 | 121.1 (5) | C17—C18—C19 | 120.6 (6) |
| C2—C3—H3 | 119.4 | C17—C18—H18 | 119.7 |
| C4—C3—H3 | 119.4 | C19—C18—H18 | 119.7 |
| C5—C4—C3 | 121.0 (5) | C20—C19—C18 | 119.1 (7) |
| C5—C4—H4 | 119.5 | C20—C19—H19 | 120.4 |
| C3—C4—H4 | 119.5 | C18—C19—H19 | 120.4 |
| C4—C5—C6 | 119.4 (5) | C21—C20—C19 | 121.4 (6) |
| C4—C5—H5 | 120.3 | C21—C20—H20 | 119.3 |
| C6—C5—H5 | 120.3 | C19—C20—H20 | 119.3 |
| C1—C6—C5 | 118.7 (4) | C20—C21—C22 | 119.9 (6) |
| C1—C6—C7 | 111.9 (4) | C20—C21—H21 | 120.0 |
| C5—C6—C7 | 129.5 (5) | C22—C21—H21 | 120.0 |
| C8—C7—C6 | 113.6 (4) | C17—C22—C21 | 119.3 (6) |
| C8—C7—H7 | 123.2 | C17—C22—H22 | 120.3 |
| C6—C7—H7 | 123.2 | C21—C22—H22 | 120.3 |
| C7—C8—C9 | 126.1 (4) | C24—C23—N1 | 115.7 (4) |
| C7—C8—S1 | 111.7 (3) | C24—C23—H23A | 108.3 |
| C9—C8—S1 | 122.2 (3) | N1—C23—H23A | 108.3 |
| C10—C9—C8 | 126.3 (5) | C24—C23—H23B | 108.3 |
| C10—C9—H9 | 116.9 | N1—C23—H23B | 108.3 |
| C8—C9—H9 | 116.9 | H23A—C23—H23B | 107.4 |
| C9—C10—C11 | 124.7 (5) | C25—C24—C23 | 177.7 (6) |
| C9—C10—H10 | 117.7 | C24—C25—C26 | 177.9 (7) |
| C11—C10—H10 | 117.7 | C25—C26—H26A | 109.5 |
| C12—C11—C16 | 117.4 (4) | C25—C26—H26B | 109.5 |
| C12—C11—C10 | 120.8 (4) | H26A—C26—H26B | 109.5 |
| C16—C11—C10 | 121.8 (4) | C25—C26—H26C | 109.5 |
| C13—C12—C11 | 122.1 (4) | H26A—C26—H26C | 109.5 |
| C13—C12—H12 | 118.9 | H26B—C26—H26C | 109.5 |
| C11—C12—H12 | 118.9 | C16—N1—C23 | 117.3 (4) |
| C14—C13—C12 | 117.6 (4) | C16—N1—S2 | 117.7 (3) |
| C14—C13—H13 | 121.2 | C23—N1—S2 | 119.1 (3) |
| C12—C13—H13 | 121.2 | C1—S1—C8 | 92.1 (2) |
| F1—C14—C15 | 118.2 (4) | O2—S2—O1 | 120.6 (2) |
| F1—C14—C13 | 118.5 (4) | O2—S2—N1 | 105.5 (2) |
| C15—C14—C13 | 123.3 (4) | O1—S2—N1 | 105.9 (2) |
| C14—C15—C16 | 118.4 (4) | O2—S2—C17 | 108.5 (2) |
| C14—C15—H15 | 120.8 | O1—S2—C17 | 107.5 (2) |
| C16—C15—H15 | 120.8 | N1—S2—C17 | 108.3 (2) |
| | | |
| C6—C1—C2—C3 | 0.2 (8) | C10—C11—C16—N1 | 1.5 (7) |
| S1—C1—C2—C3 | 180.0 (4) | C22—C17—C18—C19 | −0.9 (9) |
| C1—C2—C3—C4 | 0.1 (8) | S2—C17—C18—C19 | 177.7 (5) |
| C2—C3—C4—C5 | −0.1 (8) | C17—C18—C19—C20 | 0.3 (10) |
| C3—C4—C5—C6 | −0.2 (8) | C18—C19—C20—C21 | 0.8 (11) |
| C2—C1—C6—C5 | −0.5 (7) | C19—C20—C21—C22 | −1.1 (11) |
| S1—C1—C6—C5 | 179.7 (4) | C18—C17—C22—C21 | 0.6 (9) |
| C2—C1—C6—C7 | 179.8 (5) | S2—C17—C22—C21 | −178.0 (5) |
| S1—C1—C6—C7 | −0.1 (5) | C20—C21—C22—C17 | 0.5 (10) |
| C4—C5—C6—C1 | 0.5 (7) | C15—C16—N1—C23 | 64.9 (6) |
| C4—C5—C6—C7 | −179.8 (5) | C11—C16—N1—C23 | −115.9 (5) |
| C1—C6—C7—C8 | 0.6 (6) | C15—C16—N1—S2 | −87.9 (5) |
| C5—C6—C7—C8 | −179.0 (5) | C11—C16—N1—S2 | 91.3 (5) |
| C6—C7—C8—C9 | −179.2 (4) | C24—C23—N1—C16 | −69.7 (5) |
| C6—C7—C8—S1 | −0.9 (5) | C24—C23—N1—S2 | 82.7 (5) |
| C7—C8—C9—C10 | −173.6 (5) | C2—C1—S1—C8 | 179.8 (5) |
| S1—C8—C9—C10 | 8.3 (7) | C6—C1—S1—C8 | −0.4 (4) |
| C8—C9—C10—C11 | −176.8 (4) | C7—C8—S1—C1 | 0.7 (4) |
| C9—C10—C11—C12 | 24.6 (7) | C9—C8—S1—C1 | 179.1 (4) |
| C9—C10—C11—C16 | −158.0 (5) | C16—N1—S2—O2 | −171.5 (3) |
| C16—C11—C12—C13 | 0.5 (7) | C23—N1—S2—O2 | 36.2 (4) |
| C10—C11—C12—C13 | 178.0 (5) | C16—N1—S2—O1 | −42.6 (4) |
| C11—C12—C13—C14 | 0.2 (7) | C23—N1—S2—O1 | 165.2 (3) |
| C12—C13—C14—F1 | 178.7 (4) | C16—N1—S2—C17 | 72.5 (4) |
| C12—C13—C14—C15 | 0.4 (8) | C23—N1—S2—C17 | −79.8 (4) |
| F1—C14—C15—C16 | −180.0 (4) | C18—C17—S2—O2 | 156.6 (5) |
| C13—C14—C15—C16 | −1.6 (8) | C22—C17—S2—O2 | −24.9 (5) |
| C14—C15—C16—C11 | 2.4 (7) | C18—C17—S2—O1 | 24.6 (5) |
| C14—C15—C16—N1 | −178.4 (4) | C22—C17—S2—O1 | −156.9 (4) |
| C12—C11—C16—C15 | −1.8 (7) | C18—C17—S2—N1 | −89.4 (5) |
| C10—C11—C16—C15 | −179.3 (4) | C22—C17—S2—N1 | 89.1 (4) |
| C12—C11—C16—N1 | 179.0 (4) | | |
Hydrogen-bond geometry (Å, º) top| Cg1 is the centroid of the C1–C6 ring. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···O1i | 0.93 | 2.59 | 3.483 (7) | 162 |
| C4—H4···F1ii | 0.93 | 2.52 | 3.188 (6) | 130 |
| C18—H18···S1iii | 0.93 | 3.01 | 3.744 (6) | 137 |
| C23—H23A···Cg1iv | 0.93 | 2.69 | 3.566 (6) | 151 |
| Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−2; (iii) x, y, z+1; (iv) x+1, y, z+1. |
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