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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023006096/zn2029sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023006096/zn2029Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023006096/zn2029IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023006096/zn2029Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023006096/zn2029IIsup5.cml
Supplementary material

CCDC references: 2280606; 2280605

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](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 [sigma](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

Computing details top

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
C22H16FNO2S2F(000) = 848
Mr = 409.48Dx = 1.392 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 7.9588 (1) ÅCell parameters from 9457 reflections
b = 25.9840 (4) Åθ = 3.4–68.6°
c = 9.5178 (2) ŵ = 2.70 mm1
β = 96.853 (1)°T = 297 K
V = 1954.23 (6) Å3Block, brown
Z = 40.15 × 0.10 × 0.08 mm
Data collection top
Bruker D8 Venture Diffractometer2964 reflections with I > 2σ(I)
Radiation source: micro focus sealed tubeRint = 0.049
ω and φ scansθmax = 68.7°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 99
Tmin = 0.589, Tmax = 0.753k = 3131
44325 measured reflectionsl = 1111
3597 independent reflections
Refinement top
Refinement on F211 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H 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 reflectionsΔρmax = 0.21 e Å3
272 parametersΔρmin = 0.28 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.7141 (2)0.64416 (6)0.53276 (16)0.0782 (7)
C20.6743 (3)0.69557 (7)0.5055 (2)0.1055 (10)
H20.6114240.7049230.4207040.127*
C30.7286 (3)0.73300 (5)0.6050 (3)0.1127 (11)
H30.7019960.7673930.5868230.135*
C40.8226 (3)0.71902 (7)0.7318 (2)0.1109 (11)
H40.8589020.7440590.7984070.133*
C50.8623 (3)0.66761 (8)0.75906 (17)0.1018 (9)
H50.9252380.6582540.8438720.122*
C60.8081 (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)
H7'0.6499840.5846590.3788330.124*0.243 (4)
C8'0.790 (5)0.5504 (7)0.539 (2)0.051 (5)0.243 (4)
S10.6512 (2)0.59509 (5)0.41950 (14)0.0758 (4)0.757 (4)
C70.8282 (9)0.5758 (2)0.6526 (7)0.0900 (18)0.757 (4)
H70.8933200.5578940.7242780.108*0.757 (4)
C80.7498 (15)0.5511 (3)0.5389 (9)0.067 (3)0.757 (4)
C90.7644 (3)0.49638 (9)0.5064 (3)0.0754 (6)
H90.8082420.4744820.5790010.090*
C100.6922 (3)0.47259 (9)0.3953 (3)0.0741 (6)
H100.6328730.4929880.3259940.089*
C110.6936 (3)0.41711 (8)0.3671 (2)0.0673 (6)
C120.7752 (4)0.38326 (10)0.4678 (3)0.0976 (9)
H120.8291220.3968330.5517080.117*
C130.7790 (5)0.33108 (10)0.4481 (3)0.1019 (10)
H130.8350450.3094750.5161460.122*
C140.6980 (4)0.31212 (9)0.3256 (3)0.0837 (7)
C150.6143 (3)0.34215 (8)0.2231 (3)0.0711 (6)
H150.5579990.3275090.1415570.085*
C160.6145 (3)0.39533 (7)0.2428 (2)0.0578 (5)
C170.6983 (2)0.40434 (7)0.0853 (2)0.0545 (5)
C180.8053 (3)0.44596 (9)0.0912 (3)0.0739 (6)
H180.7707510.4788860.0691610.089*
C190.9636 (3)0.43766 (13)0.1303 (3)0.0927 (8)
H191.0374220.4651990.1345870.111*
C201.0139 (3)0.38892 (15)0.1632 (3)0.0947 (9)
H201.1212590.3837770.1898820.114*
C210.9072 (4)0.34806 (12)0.1569 (3)0.0888 (8)
H210.9422940.3152100.1791190.107*
C220.7481 (3)0.35538 (9)0.1179 (2)0.0689 (6)
H220.6750160.3276570.1136420.083*
N10.5283 (2)0.42741 (6)0.1368 (2)0.0616 (4)
O10.40697 (18)0.36642 (5)0.05058 (18)0.0706 (4)
O20.42235 (19)0.45927 (5)0.09632 (17)0.0674 (4)
F10.6977 (3)0.26050 (5)0.3036 (2)0.1171 (6)
S20.49738 (6)0.41360 (2)0.03136 (6)0.05557 (17)
H1N0.545 (3)0.4587 (6)0.147 (2)0.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0989 (18)0.0723 (15)0.0687 (14)0.0213 (13)0.0318 (13)0.0024 (12)
C20.132 (3)0.0839 (19)0.103 (2)0.0145 (18)0.0231 (19)0.0204 (17)
C30.135 (3)0.0621 (16)0.149 (3)0.0154 (17)0.052 (3)0.0014 (19)
C40.135 (3)0.081 (2)0.126 (3)0.0312 (19)0.054 (2)0.0337 (19)
C50.124 (2)0.099 (2)0.0829 (18)0.0240 (19)0.0139 (17)0.0201 (16)
C60.0929 (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)
S10.1095 (10)0.0607 (5)0.0576 (8)0.0079 (5)0.0109 (6)0.0006 (4)
C70.111 (4)0.077 (3)0.076 (4)0.003 (2)0.010 (3)0.000 (3)
C80.065 (6)0.067 (3)0.071 (3)0.009 (2)0.017 (2)0.003 (2)
C90.0896 (17)0.0647 (14)0.0712 (14)0.0018 (12)0.0068 (12)0.0001 (11)
C100.1028 (18)0.0551 (12)0.0632 (13)0.0022 (12)0.0055 (12)0.0060 (10)
C110.0864 (15)0.0516 (11)0.0647 (13)0.0000 (10)0.0123 (11)0.0086 (10)
C120.142 (3)0.0674 (16)0.0772 (17)0.0011 (16)0.0111 (17)0.0139 (13)
C130.141 (3)0.0651 (16)0.095 (2)0.0093 (16)0.0046 (19)0.0296 (15)
C140.114 (2)0.0459 (12)0.0930 (19)0.0051 (12)0.0186 (16)0.0146 (12)
C150.0888 (16)0.0472 (11)0.0783 (15)0.0022 (11)0.0142 (12)0.0065 (10)
C160.0645 (12)0.0457 (10)0.0658 (12)0.0025 (9)0.0186 (10)0.0083 (9)
C170.0545 (10)0.0502 (10)0.0561 (11)0.0008 (8)0.0041 (8)0.0033 (8)
C180.0654 (13)0.0673 (14)0.0871 (16)0.0139 (11)0.0014 (12)0.0091 (12)
C190.0671 (15)0.116 (2)0.0935 (19)0.0253 (16)0.0020 (14)0.0039 (17)
C200.0562 (14)0.147 (3)0.0796 (17)0.0120 (17)0.0026 (12)0.0036 (18)
C210.0794 (17)0.096 (2)0.0904 (19)0.0269 (15)0.0098 (14)0.0087 (15)
C220.0724 (14)0.0582 (12)0.0752 (14)0.0077 (10)0.0049 (11)0.0050 (11)
N10.0745 (11)0.0401 (8)0.0700 (11)0.0070 (8)0.0081 (9)0.0009 (8)
O10.0613 (8)0.0459 (7)0.1008 (12)0.0087 (6)0.0061 (8)0.0028 (7)
O20.0711 (9)0.0437 (7)0.0826 (10)0.0098 (6)0.0111 (7)0.0015 (7)
F10.1731 (17)0.0454 (8)0.1300 (14)0.0126 (9)0.0067 (12)0.0189 (8)
S20.0546 (3)0.0379 (2)0.0718 (3)0.00112 (18)0.0029 (2)0.0018 (2)
Geometric parameters (Å, º) top
C1—C21.3900C11—C121.402 (3)
C1—C61.3900C12—C131.369 (4)
C1—C7'1.531 (14)C12—H120.9300
C1—S11.7058 (18)C13—C141.356 (4)
C2—C31.3900C13—H130.9300
C2—H20.9300C14—F11.358 (3)
C3—C41.3900C14—C151.360 (3)
C3—H30.9300C15—C161.394 (3)
C4—C51.3900C15—H150.9300
C4—H40.9300C16—N11.421 (3)
C5—C61.3900C17—C221.379 (3)
C5—H50.9300C17—C181.381 (3)
C6—C71.426 (6)C17—S21.754 (2)
C6—S1'1.727 (5)C18—C191.373 (4)
S1'—C8'1.738 (17)C18—H180.9300
C7'—C8'1.356 (18)C19—C201.375 (4)
C7'—H7'0.9300C19—H190.9300
C8'—C91.446 (17)C20—C211.365 (4)
S1—C81.732 (7)C20—H200.9300
C7—C81.345 (8)C21—C221.375 (4)
C7—H70.9300C21—H210.9300
C8—C91.463 (7)C22—H220.9300
C9—C101.298 (3)N1—S21.6301 (19)
C9—H90.9300N1—H1N0.828 (16)
C10—C111.467 (3)O1—S21.4222 (14)
C10—H100.9300O2—S21.4348 (14)
C11—C161.393 (3)
C2—C1—C6120.0C16—C11—C10122.8 (2)
C2—C1—C7'144.2 (7)C12—C11—C10120.3 (2)
C6—C1—C7'95.5 (7)C13—C12—C11122.9 (3)
C2—C1—S1123.88 (12)C13—C12—H12118.5
C6—C1—S1116.11 (12)C11—C12—H12118.5
C3—C2—C1120.0C14—C13—C12117.5 (3)
C3—C2—H2120.0C14—C13—H13121.3
C1—C2—H2120.0C12—C13—H13121.3
C2—C3—C4120.0C13—C14—F1118.9 (2)
C2—C3—H3120.0C13—C14—C15123.4 (2)
C4—C3—H3120.0F1—C14—C15117.7 (3)
C5—C4—C3120.0C14—C15—C16118.6 (2)
C5—C4—H4120.0C14—C15—H15120.7
C3—C4—H4120.0C16—C15—H15120.7
C4—C5—C6120.0C11—C16—C15120.7 (2)
C4—C5—H5120.0C11—C16—N1119.74 (18)
C6—C5—H5120.0C15—C16—N1119.6 (2)
C5—C6—C1120.0C22—C17—C18121.2 (2)
C5—C6—C7134.3 (3)C22—C17—S2119.30 (17)
C1—C6—C7105.7 (3)C18—C17—S2119.49 (17)
C5—C6—S1'114.1 (2)C19—C18—C17118.5 (2)
C1—C6—S1'125.9 (2)C19—C18—H18120.7
C6—S1'—C8'86.1 (6)C17—C18—H18120.7
C8'—C7'—C1120.6 (13)C18—C19—C20120.5 (3)
C8'—C7'—H7'119.7C18—C19—H19119.7
C1—C7'—H7'119.7C20—C19—H19119.7
C7'—C8'—C9126.0 (15)C21—C20—C19120.5 (3)
C7'—C8'—S1'110.9 (13)C21—C20—H20119.8
C9—C8'—S1'119.1 (13)C19—C20—H20119.8
C1—S1—C890.1 (2)C20—C21—C22120.1 (3)
C8—C7—C6117.7 (6)C20—C21—H21119.9
C8—C7—H7121.1C22—C21—H21119.9
C6—C7—H7121.1C21—C22—C17119.2 (2)
C7—C8—C9126.3 (6)C21—C22—H22120.4
C7—C8—S1110.1 (5)C17—C22—H22120.4
C9—C8—S1122.9 (5)C16—N1—S2124.85 (14)
C10—C9—C8'132.4 (8)C16—N1—H1N116.0 (16)
C10—C9—C8126.6 (4)S2—N1—H1N109.5 (16)
C10—C9—H9113.8O1—S2—O2118.64 (9)
C8'—C9—H9113.8O1—S2—N1109.32 (10)
C9—C10—C11127.2 (2)O2—S2—N1104.32 (9)
C9—C10—H10116.4O1—S2—C17108.01 (9)
C11—C10—H10116.4O2—S2—C17109.55 (10)
C16—C11—C12116.8 (2)N1—S2—C17106.35 (9)
C6—C1—C2—C30.0C8'—C9—C10—C11171 (2)
C7'—C1—C2—C3171.5 (14)C8—C9—C10—C11174.3 (7)
S1—C1—C2—C3178.91 (16)C9—C10—C11—C16178.7 (3)
C1—C2—C3—C40.0C9—C10—C11—C122.1 (4)
C2—C3—C4—C50.0C16—C11—C12—C130.1 (5)
C3—C4—C5—C60.0C10—C11—C12—C13179.2 (3)
C4—C5—C6—C10.0C11—C12—C13—C140.7 (5)
C4—C5—C6—C7178.8 (4)C12—C13—C14—F1179.2 (3)
C4—C5—C6—S1'179.6 (2)C12—C13—C14—C150.1 (5)
C2—C1—C6—C50.0C13—C14—C15—C161.5 (4)
C7'—C1—C6—C5175.0 (8)F1—C14—C15—C16179.3 (2)
S1—C1—C6—C5178.99 (15)C12—C11—C16—C151.6 (4)
C2—C1—C6—C7179.1 (3)C10—C11—C16—C15177.7 (2)
S1—C1—C6—C71.9 (3)C12—C11—C16—N1179.5 (2)
C2—C1—C6—S1'179.5 (3)C10—C11—C16—N10.2 (3)
C7'—C1—C6—S1'5.5 (8)C14—C15—C16—C112.3 (4)
C5—C6—S1'—C8'171.8 (13)C14—C15—C16—N1179.8 (2)
C1—C6—S1'—C8'8.7 (14)C22—C17—C18—C190.1 (4)
C2—C1—C7'—C8'171 (2)S2—C17—C18—C19178.41 (19)
C6—C1—C7'—C8'2 (3)C17—C18—C19—C200.2 (4)
C1—C7'—C8'—C9165 (2)C18—C19—C20—C210.2 (4)
C1—C7'—C8'—S1'8 (4)C19—C20—C21—C220.2 (4)
C6—S1'—C8'—C7'8 (2)C20—C21—C22—C170.1 (4)
C6—S1'—C8'—C9167 (3)C18—C17—C22—C210.0 (4)
C2—C1—S1—C8178.8 (5)S2—C17—C22—C21178.48 (19)
C6—C1—S1—C80.1 (5)C11—C16—N1—S2153.99 (18)
C5—C6—C7—C8177.3 (7)C15—C16—N1—S228.1 (3)
C1—C6—C7—C83.8 (9)C16—N1—S2—O158.1 (2)
C6—C7—C8—C9175.1 (8)C16—N1—S2—O2174.05 (17)
C6—C7—C8—S14.0 (11)C16—N1—S2—C1758.28 (19)
C1—S1—C8—C72.2 (8)C22—C17—S2—O18.2 (2)
C1—S1—C8—C9173.7 (9)C18—C17—S2—O1173.24 (18)
C7'—C8'—C9—C1015 (5)C22—C17—S2—O2138.77 (17)
S1'—C8'—C9—C10170.8 (10)C18—C17—S2—O242.7 (2)
C7—C8—C9—C10178.3 (8)C22—C17—S2—N1109.03 (18)
S1—C8—C9—C108.4 (13)C18—C17—S2—N169.51 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O10.932.302.980 (3)130
C10—H10···02i0.932.513.383 (3)157
N1—H1N···O2i0.83 (2)2.21 (2)3.001 (2)161 (2)
C22—H22···F1ii0.932.443.116 (3)130
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1/2, z1/2.
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide (II) top
Crystal data top
C26H20FNO2S2F(000) = 960
Mr = 461.55Dx = 1.327 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 9.3517 (3) ÅCell parameters from 3616 reflections
b = 31.7075 (11) Åθ = 2.8–65.4°
c = 8.6063 (3) ŵ = 2.35 mm1
β = 115.179 (2)°T = 297 K
V = 2309.45 (14) Å3Solid, white
Z = 40.11 × 0.07 × 0.02 mm
Data collection top
Bruker D8 Venture Diffractometer2098 reflections with I > 2σ(I)
Radiation source: micro focus sealed tubeRint = 0.155
ω and φ scansθmax = 68.8°, θmin = 5.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1111
Tmin = 0.604, Tmax = 0.753k = 3738
39443 measured reflectionsl = 1010
4270 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.00Δρmax = 0.33 e Å3
4270 reflectionsΔρmin = 0.37 e Å3
291 parametersExtinction correction: SHELXL-2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction 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
xyzUiso*/Ueq
C10.2549 (6)0.32808 (15)0.0285 (6)0.0669 (12)
C20.2360 (6)0.33934 (17)0.1918 (6)0.0778 (14)
H20.3119000.3555780.2070420.093*
C30.1029 (7)0.32600 (17)0.3309 (7)0.0825 (15)
H30.0890650.3333200.4410410.099*
C40.0110 (6)0.30184 (16)0.3096 (6)0.0763 (14)
H40.1000100.2932490.4056770.092*
C50.0054 (6)0.29044 (15)0.1498 (6)0.0722 (13)
H50.0719510.2743080.1370150.087*
C60.1408 (5)0.30337 (14)0.0042 (5)0.0626 (11)
C70.1836 (6)0.29535 (14)0.1732 (6)0.0673 (12)
H70.1221200.2793210.2120830.081*
C80.3227 (5)0.31338 (13)0.2798 (5)0.0609 (11)
C90.3969 (6)0.31034 (15)0.4648 (6)0.0682 (12)
H90.3503120.2922420.5148470.082*
C100.5265 (6)0.33107 (14)0.5712 (6)0.0633 (12)
H100.5710840.3503310.5231680.076*
C110.6030 (5)0.32555 (13)0.7581 (5)0.0586 (11)
C120.5852 (6)0.28800 (14)0.8336 (6)0.0659 (12)
H120.5212740.2668250.7636000.079*
C130.6595 (6)0.28137 (15)1.0084 (6)0.0702 (13)
H130.6468160.2562231.0567350.084*
C140.7527 (6)0.31322 (16)1.1085 (6)0.0718 (13)
C150.7743 (6)0.35085 (15)1.0435 (6)0.0694 (13)
H150.8363000.3719591.1158420.083*
C160.7016 (5)0.35672 (13)0.8677 (5)0.0585 (11)
C170.6526 (6)0.45543 (14)0.9821 (6)0.0688 (13)
C180.5818 (8)0.43930 (18)1.0789 (7)0.0899 (17)
H180.5055810.4183551.0335460.108*
C190.6226 (9)0.4539 (2)1.2444 (9)0.106 (2)
H190.5745030.4427861.3102780.128*
C200.7344 (9)0.4848 (2)1.3093 (9)0.109 (2)
H200.7629460.4944151.4206230.131*
C210.8042 (9)0.5017 (2)1.2151 (9)0.109 (2)
H210.8786240.5230521.2608680.130*
C220.7647 (7)0.48710 (16)1.0491 (7)0.0872 (16)
H220.8129800.4984740.9838360.105*
C230.8877 (6)0.40504 (16)0.8143 (7)0.0763 (14)
H23A0.9254730.3808350.7736230.092*
H23B0.8826480.4286750.7405000.092*
C241.0039 (6)0.41494 (15)0.9891 (7)0.0764 (14)
C251.0953 (7)0.42202 (17)1.1328 (8)0.0886 (17)
C261.2031 (8)0.4310 (2)1.3114 (8)0.117 (2)
H26A1.1430240.4381141.3745900.175*
H26B1.2703750.4542141.3152340.175*
H26C1.2665160.4065451.3616370.175*
N10.7255 (4)0.39583 (10)0.7947 (5)0.0613 (10)
O10.4505 (4)0.41733 (11)0.7156 (4)0.0851 (11)
O20.6400 (5)0.46681 (11)0.6790 (5)0.0949 (12)
S10.40923 (16)0.34048 (5)0.16627 (16)0.0776 (5)
S20.60508 (16)0.43535 (4)0.77698 (15)0.0715 (4)
F10.8245 (4)0.30760 (10)1.2817 (3)0.0982 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.060 (3)0.078 (3)0.063 (3)0.003 (2)0.026 (2)0.005 (2)
C20.073 (3)0.097 (4)0.066 (3)0.005 (3)0.033 (3)0.000 (3)
C30.080 (4)0.107 (4)0.059 (3)0.005 (3)0.029 (3)0.003 (3)
C40.074 (3)0.089 (3)0.062 (3)0.001 (3)0.025 (3)0.013 (2)
C50.063 (3)0.079 (3)0.066 (3)0.008 (2)0.019 (2)0.013 (2)
C60.060 (3)0.071 (3)0.056 (2)0.001 (2)0.024 (2)0.008 (2)
C70.065 (3)0.072 (3)0.065 (3)0.015 (2)0.028 (2)0.005 (2)
C80.063 (3)0.064 (2)0.057 (2)0.005 (2)0.027 (2)0.003 (2)
C90.068 (3)0.071 (3)0.061 (3)0.007 (2)0.023 (2)0.004 (2)
C100.064 (3)0.065 (3)0.059 (2)0.001 (2)0.025 (2)0.000 (2)
C110.057 (3)0.061 (2)0.057 (2)0.000 (2)0.024 (2)0.0004 (19)
C120.068 (3)0.064 (3)0.066 (3)0.003 (2)0.029 (2)0.000 (2)
C130.076 (3)0.070 (3)0.067 (3)0.000 (3)0.034 (3)0.007 (2)
C140.079 (3)0.081 (3)0.049 (2)0.007 (3)0.021 (2)0.009 (2)
C150.070 (3)0.070 (3)0.060 (3)0.001 (2)0.020 (2)0.001 (2)
C160.062 (3)0.056 (2)0.057 (2)0.002 (2)0.025 (2)0.0017 (18)
C170.076 (3)0.063 (3)0.070 (3)0.003 (2)0.033 (3)0.001 (2)
C180.107 (5)0.085 (3)0.081 (4)0.009 (3)0.044 (3)0.010 (3)
C190.132 (6)0.106 (4)0.096 (5)0.003 (4)0.063 (4)0.003 (4)
C200.134 (6)0.110 (5)0.079 (4)0.016 (5)0.042 (4)0.019 (4)
C210.119 (5)0.096 (4)0.099 (5)0.019 (4)0.034 (4)0.035 (4)
C220.099 (4)0.072 (3)0.088 (4)0.016 (3)0.038 (3)0.014 (3)
C230.074 (3)0.076 (3)0.081 (3)0.009 (3)0.035 (3)0.005 (2)
C240.068 (3)0.068 (3)0.090 (4)0.008 (3)0.031 (3)0.005 (3)
C250.081 (4)0.075 (3)0.101 (4)0.008 (3)0.030 (3)0.008 (3)
C260.102 (5)0.123 (5)0.093 (4)0.012 (4)0.010 (4)0.015 (4)
N10.064 (2)0.0555 (19)0.061 (2)0.0017 (17)0.0238 (18)0.0022 (16)
O10.062 (2)0.084 (2)0.088 (2)0.0006 (18)0.0117 (18)0.0075 (18)
O20.139 (3)0.0680 (19)0.077 (2)0.000 (2)0.045 (2)0.0174 (17)
S10.0655 (8)0.0998 (9)0.0656 (7)0.0180 (7)0.0261 (6)0.0056 (6)
S20.0822 (9)0.0616 (6)0.0625 (7)0.0020 (6)0.0229 (6)0.0030 (5)
F10.114 (2)0.107 (2)0.0552 (16)0.0063 (19)0.0187 (16)0.0166 (15)
Geometric parameters (Å, º) top
C1—C21.387 (7)C15—C161.382 (6)
C1—C61.409 (7)C15—H150.9300
C1—S11.729 (5)C16—N11.450 (5)
C2—C31.376 (7)C17—C181.365 (7)
C2—H20.9300C17—C221.387 (7)
C3—C41.386 (7)C17—S21.747 (5)
C3—H30.9300C18—C191.388 (8)
C4—C51.367 (7)C18—H180.9300
C4—H40.9300C19—C201.368 (9)
C5—C61.411 (6)C19—H190.9300
C5—H50.9300C20—C211.349 (9)
C6—C71.426 (6)C20—H200.9300
C7—C81.358 (6)C21—C221.394 (8)
C7—H70.9300C21—H210.9300
C8—C91.444 (6)C22—H220.9300
C8—S11.738 (5)C23—C241.467 (7)
C9—C101.340 (6)C23—N11.483 (6)
C9—H90.9300C23—H23A0.9700
C10—C111.466 (6)C23—H23B0.9700
C10—H100.9300C24—C251.188 (7)
C11—C121.400 (6)C25—C261.464 (8)
C11—C161.406 (6)C26—H26A0.9600
C12—C131.378 (6)C26—H26B0.9600
C12—H120.9300C26—H26C0.9600
C13—C141.372 (7)N1—S21.648 (4)
C13—H130.9300O1—S21.431 (4)
C14—F11.361 (5)O2—S21.431 (4)
C14—C151.369 (7)
C2—C1—C6121.0 (4)C15—C16—C11121.1 (4)
C2—C1—S1128.2 (4)C15—C16—N1119.7 (4)
C6—C1—S1110.8 (3)C11—C16—N1119.2 (4)
C3—C2—C1118.7 (5)C18—C17—C22119.6 (5)
C3—C2—H2120.6C18—C17—S2119.9 (4)
C1—C2—H2120.6C22—C17—S2120.4 (4)
C2—C3—C4121.1 (5)C17—C18—C19120.6 (6)
C2—C3—H3119.4C17—C18—H18119.7
C4—C3—H3119.4C19—C18—H18119.7
C5—C4—C3121.0 (5)C20—C19—C18119.1 (7)
C5—C4—H4119.5C20—C19—H19120.4
C3—C4—H4119.5C18—C19—H19120.4
C4—C5—C6119.4 (5)C21—C20—C19121.4 (6)
C4—C5—H5120.3C21—C20—H20119.3
C6—C5—H5120.3C19—C20—H20119.3
C1—C6—C5118.7 (4)C20—C21—C22119.9 (6)
C1—C6—C7111.9 (4)C20—C21—H21120.0
C5—C6—C7129.5 (5)C22—C21—H21120.0
C8—C7—C6113.6 (4)C17—C22—C21119.3 (6)
C8—C7—H7123.2C17—C22—H22120.3
C6—C7—H7123.2C21—C22—H22120.3
C7—C8—C9126.1 (4)C24—C23—N1115.7 (4)
C7—C8—S1111.7 (3)C24—C23—H23A108.3
C9—C8—S1122.2 (3)N1—C23—H23A108.3
C10—C9—C8126.3 (5)C24—C23—H23B108.3
C10—C9—H9116.9N1—C23—H23B108.3
C8—C9—H9116.9H23A—C23—H23B107.4
C9—C10—C11124.7 (5)C25—C24—C23177.7 (6)
C9—C10—H10117.7C24—C25—C26177.9 (7)
C11—C10—H10117.7C25—C26—H26A109.5
C12—C11—C16117.4 (4)C25—C26—H26B109.5
C12—C11—C10120.8 (4)H26A—C26—H26B109.5
C16—C11—C10121.8 (4)C25—C26—H26C109.5
C13—C12—C11122.1 (4)H26A—C26—H26C109.5
C13—C12—H12118.9H26B—C26—H26C109.5
C11—C12—H12118.9C16—N1—C23117.3 (4)
C14—C13—C12117.6 (4)C16—N1—S2117.7 (3)
C14—C13—H13121.2C23—N1—S2119.1 (3)
C12—C13—H13121.2C1—S1—C892.1 (2)
F1—C14—C15118.2 (4)O2—S2—O1120.6 (2)
F1—C14—C13118.5 (4)O2—S2—N1105.5 (2)
C15—C14—C13123.3 (4)O1—S2—N1105.9 (2)
C14—C15—C16118.4 (4)O2—S2—C17108.5 (2)
C14—C15—H15120.8O1—S2—C17107.5 (2)
C16—C15—H15120.8N1—S2—C17108.3 (2)
C6—C1—C2—C30.2 (8)C10—C11—C16—N11.5 (7)
S1—C1—C2—C3180.0 (4)C22—C17—C18—C190.9 (9)
C1—C2—C3—C40.1 (8)S2—C17—C18—C19177.7 (5)
C2—C3—C4—C50.1 (8)C17—C18—C19—C200.3 (10)
C3—C4—C5—C60.2 (8)C18—C19—C20—C210.8 (11)
C2—C1—C6—C50.5 (7)C19—C20—C21—C221.1 (11)
S1—C1—C6—C5179.7 (4)C18—C17—C22—C210.6 (9)
C2—C1—C6—C7179.8 (5)S2—C17—C22—C21178.0 (5)
S1—C1—C6—C70.1 (5)C20—C21—C22—C170.5 (10)
C4—C5—C6—C10.5 (7)C15—C16—N1—C2364.9 (6)
C4—C5—C6—C7179.8 (5)C11—C16—N1—C23115.9 (5)
C1—C6—C7—C80.6 (6)C15—C16—N1—S287.9 (5)
C5—C6—C7—C8179.0 (5)C11—C16—N1—S291.3 (5)
C6—C7—C8—C9179.2 (4)C24—C23—N1—C1669.7 (5)
C6—C7—C8—S10.9 (5)C24—C23—N1—S282.7 (5)
C7—C8—C9—C10173.6 (5)C2—C1—S1—C8179.8 (5)
S1—C8—C9—C108.3 (7)C6—C1—S1—C80.4 (4)
C8—C9—C10—C11176.8 (4)C7—C8—S1—C10.7 (4)
C9—C10—C11—C1224.6 (7)C9—C8—S1—C1179.1 (4)
C9—C10—C11—C16158.0 (5)C16—N1—S2—O2171.5 (3)
C16—C11—C12—C130.5 (7)C23—N1—S2—O236.2 (4)
C10—C11—C12—C13178.0 (5)C16—N1—S2—O142.6 (4)
C11—C12—C13—C140.2 (7)C23—N1—S2—O1165.2 (3)
C12—C13—C14—F1178.7 (4)C16—N1—S2—C1772.5 (4)
C12—C13—C14—C150.4 (8)C23—N1—S2—C1779.8 (4)
F1—C14—C15—C16180.0 (4)C18—C17—S2—O2156.6 (5)
C13—C14—C15—C161.6 (8)C22—C17—S2—O224.9 (5)
C14—C15—C16—C112.4 (7)C18—C17—S2—O124.6 (5)
C14—C15—C16—N1178.4 (4)C22—C17—S2—O1156.9 (4)
C12—C11—C16—C151.8 (7)C18—C17—S2—N189.4 (5)
C10—C11—C16—C15179.3 (4)C22—C17—S2—N189.1 (4)
C12—C11—C16—N1179.0 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.593.483 (7)162
C4—H4···F1ii0.932.523.188 (6)130
C18—H18···S1iii0.933.013.744 (6)137
C23—H23A···Cg1iv0.932.693.566 (6)151
Symmetry codes: (i) x, y, z1; (ii) x1, y, z2; (iii) x, y, z+1; (iv) x+1, y, z+1.
 

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