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Four closely related N-(3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phen-2-yl)benzamides, bearing different substituents on the benzamide ring, have been synthesized and structurally characterized. In each of N-(3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phen-2-yl)-3-fluoro­benzamide, C22H18FNO2S, (I), N-(3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phen-2-yl)-4-chloro­benzamide, C22H18ClNO2S, (II), N-(3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phen-2-yl)-2,6-di­fluoro­benzamide, C22H17F2NO2S, (III), and N-(3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phen-2-yl)-2-meth­oxy­benzamide, C23H21NO3S, (IV), the last of which crystallizes with Z′ = 2 in the space group P\overline{1}, the fused six-membered ring adopts a half-chair conformation. In each of (I)–(III), this ring is disordered over two sets of atomic sites having occupancies of 0.811 (6) and 0.189 (6) in (I), 0.645 (7) and 0.355 (7) in (II), and 0.784 (6) and 0.216 (6) in (III), such that the two disorder components of the ring are almost enanti­omeric. Mol­ecules of (I) are linked into chains by π–π stacking inter­actions, and those of (II) are linked into chains by a C—H...π hydrogen bond. A combination of two C—H...O hydrogen bonds and two C—H...π hydrogen bonds links the mol­ecules of (III) into complex sheets, but the mol­ecules of (IV) are linked by a combination of two hydrogen bonds, one each of the C—H...O and C—H...π types, to form centrosymmetric tetra­mers. The structures of (I)–(IV) are compared with that of the unsubstituted analogue N-(3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phen-2-yl)benzamide and a new refinement of the parent amine 2-amino-3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phene, using the original data set, has found that here too the fused six-membered ring exhibits conformational disorder, with occupancies of 0.887 (9) and 0.113 (9). Comparisons are made with some related compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017326/ov3102sup1.cif
Contains datablocks global, I, II, III, IV, VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102IVsup5.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102VIsup6.hkl
Contains datablock VI

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017326/ov3102Isup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017326/ov3102IIsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017326/ov3102IIIsup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017326/ov3102VIsup10.cml
Supplementary material

CCDC references: 1588989; 1588988; 1588987; 1588986; 1588985

Computing details top

Data collection: APEX2 (Bruker, 2012) for (I), (II), (III), (IV); CrysAlis PRO (Agilent, 2012) for (VI). Cell refinement: APEX2 (Bruker, 2012) for (I), (II), (III), (IV); CrysAlis PRO (Agilent, 2012) for (VI). Data reduction: SAINT-Plus (Bruker, 2012) for (I), (II), (III), (IV); CrysAlis RED (Agilent, 2012) for (VI). For all structures, program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-3-fluorobenzamide (I) top
Crystal data top
C22H18FNO2SF(000) = 792
Mr = 379.43Dx = 1.371 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.9489 (11) ÅCell parameters from 5442 reflections
b = 7.2739 (4) Åθ = 1.3–30.3°
c = 15.9222 (10) ŵ = 0.20 mm1
β = 95.813 (4)°T = 296 K
V = 1837.6 (2) Å3Block, colourless
Z = 40.15 × 0.10 × 0.10 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2343 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.052
φ and ω scansθmax = 26.6°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 2020
Tmin = 0.895, Tmax = 0.980k = 99
21151 measured reflectionsl = 2020
3809 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0475P)2 + 0.4981P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.16 e Å3
3809 reflectionsΔρmin = 0.20 e Å3
258 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
12 restraintsExtinction coefficient: 0.0080 (9)
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)
C70.47949 (13)0.6101 (3)0.23133 (15)0.0465 (6)
O70.44771 (10)0.6398 (3)0.15993 (11)0.0692 (5)
C10.42894 (13)0.6016 (3)0.30528 (14)0.0429 (5)
C20.34324 (14)0.5665 (3)0.28845 (16)0.0532 (6)
H20.31920.54670.23350.064*
C30.29523 (14)0.5618 (3)0.35488 (19)0.0583 (7)
F30.21131 (9)0.5261 (3)0.33825 (12)0.0938 (6)
C40.32656 (16)0.5938 (3)0.43705 (18)0.0589 (7)
H40.29200.58970.48060.071*
C50.41083 (15)0.6321 (3)0.45229 (17)0.0587 (7)
H50.43410.65630.50710.070*
C60.46162 (14)0.6352 (3)0.38704 (15)0.0514 (6)
H60.51880.66030.39860.062*
N10.56415 (10)0.5827 (2)0.24788 (11)0.0451 (5)
H10.58370.56290.29940.054*
S110.59028 (4)0.62223 (8)0.08302 (4)0.0539 (2)
C120.62066 (14)0.5844 (3)0.18772 (13)0.0409 (5)
C130.70640 (13)0.5546 (3)0.20427 (13)0.0395 (5)
C13A0.74750 (14)0.5566 (3)0.12712 (14)0.0434 (5)0.811 (6)
C140.8387 (2)0.5147 (13)0.1187 (2)0.0586 (11)0.811 (6)
H14A0.85750.41660.15740.070*0.811 (6)
H14B0.87260.62270.13390.070*0.811 (6)
C150.8513 (2)0.4569 (6)0.0284 (2)0.0694 (12)0.811 (6)
H15A0.91100.45030.02180.083*0.811 (6)
H15B0.82690.33620.01680.083*0.811 (6)
C160.8092 (3)0.5961 (6)0.0331 (2)0.0761 (13)0.811 (6)
H16A0.82270.56770.08970.091*0.811 (6)
H16B0.83070.71790.01860.091*0.811 (6)
C170.7135 (3)0.5940 (16)0.0311 (2)0.0714 (10)0.811 (6)
H17A0.68890.70170.05990.086*0.811 (6)
H17B0.68990.48570.06010.086*0.811 (6)
C17A0.69285 (15)0.5931 (3)0.05883 (14)0.0506 (6)0.811 (6)
C23A0.74750 (14)0.5566 (3)0.12712 (14)0.0434 (5)0.189 (6)
C240.8348 (9)0.495 (6)0.1092 (7)0.0586 (11)0.189 (6)
H24A0.83840.36240.11340.070*0.189 (6)
H24B0.87620.54690.15160.070*0.189 (6)
C250.8558 (7)0.555 (3)0.0216 (8)0.0694 (12)0.189 (6)
H25A0.86450.68670.02130.083*0.189 (6)
H25B0.90780.49610.00930.083*0.189 (6)
C260.7861 (8)0.505 (2)0.0465 (7)0.0761 (13)0.189 (6)
H26A0.77480.37360.04470.091*0.189 (6)
H26B0.80340.53370.10170.091*0.189 (6)
C270.7063 (13)0.613 (7)0.0321 (6)0.0714 (10)0.189 (6)
H27A0.71320.74110.04610.086*0.189 (6)
H27B0.65830.56420.06750.086*0.189 (6)
C27A0.69285 (15)0.5931 (3)0.05883 (14)0.0506 (6)0.189 (6)
C370.74366 (14)0.5196 (3)0.29015 (14)0.0456 (5)
O370.69952 (10)0.4827 (3)0.34774 (10)0.0662 (5)
C310.83655 (14)0.5287 (3)0.31342 (14)0.0490 (6)
C320.87614 (17)0.3885 (4)0.36015 (17)0.0771 (9)
H320.84570.28540.37350.093*
C330.9610 (2)0.4007 (6)0.3872 (2)0.1091 (13)
H330.98780.30520.41820.131*
C341.0054 (2)0.5528 (7)0.3686 (2)0.1112 (14)
H341.06250.56040.38690.133*
C350.96709 (19)0.6936 (6)0.3235 (2)0.0901 (11)
H350.99780.79740.31160.108*
C360.88298 (16)0.6819 (4)0.29559 (16)0.0633 (7)
H360.85690.77790.26440.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C70.0376 (13)0.0436 (13)0.0566 (15)0.0011 (10)0.0027 (11)0.0005 (11)
O70.0486 (10)0.0989 (14)0.0582 (11)0.0068 (10)0.0046 (8)0.0119 (10)
C10.0333 (12)0.0363 (12)0.0578 (14)0.0029 (9)0.0017 (10)0.0025 (10)
C20.0380 (13)0.0541 (14)0.0658 (16)0.0034 (11)0.0026 (12)0.0075 (12)
C30.0309 (13)0.0537 (15)0.091 (2)0.0032 (11)0.0084 (13)0.0069 (14)
F30.0362 (8)0.1247 (14)0.1210 (14)0.0057 (9)0.0103 (9)0.0185 (11)
C40.0507 (15)0.0548 (15)0.0740 (18)0.0080 (12)0.0201 (14)0.0036 (13)
C50.0536 (16)0.0597 (16)0.0629 (16)0.0043 (13)0.0067 (13)0.0094 (12)
C60.0373 (13)0.0534 (14)0.0625 (16)0.0019 (11)0.0002 (11)0.0063 (12)
N10.0354 (10)0.0538 (11)0.0451 (11)0.0001 (8)0.0001 (8)0.0001 (9)
S110.0551 (4)0.0550 (4)0.0494 (4)0.0035 (3)0.0051 (3)0.0073 (3)
C120.0440 (13)0.0354 (11)0.0428 (12)0.0034 (9)0.0029 (10)0.0009 (9)
C130.0385 (12)0.0385 (12)0.0415 (12)0.0032 (9)0.0043 (10)0.0021 (9)
C13A0.0491 (14)0.0389 (12)0.0430 (13)0.0039 (10)0.0083 (11)0.0010 (10)
C140.0567 (17)0.069 (2)0.0538 (17)0.0025 (14)0.0213 (14)0.0051 (17)
C150.072 (2)0.081 (3)0.0596 (19)0.006 (2)0.0288 (16)0.013 (2)
C160.105 (3)0.073 (3)0.056 (2)0.006 (2)0.033 (2)0.008 (2)
C170.091 (2)0.079 (3)0.0439 (15)0.0127 (19)0.0082 (14)0.0074 (14)
C17A0.0610 (15)0.0470 (13)0.0438 (13)0.0063 (11)0.0054 (11)0.0013 (11)
C23A0.0491 (14)0.0389 (12)0.0430 (13)0.0039 (10)0.0083 (11)0.0010 (10)
C240.0567 (17)0.069 (2)0.0538 (17)0.0025 (14)0.0213 (14)0.0051 (17)
C250.072 (2)0.081 (3)0.0596 (19)0.006 (2)0.0288 (16)0.013 (2)
C260.105 (3)0.073 (3)0.056 (2)0.006 (2)0.033 (2)0.008 (2)
C270.091 (2)0.079 (3)0.0439 (15)0.0127 (19)0.0082 (14)0.0074 (14)
C27A0.0610 (15)0.0470 (13)0.0438 (13)0.0063 (11)0.0054 (11)0.0013 (11)
C370.0417 (13)0.0507 (13)0.0449 (13)0.0004 (11)0.0069 (11)0.0020 (11)
O370.0436 (10)0.1099 (15)0.0458 (10)0.0053 (9)0.0081 (8)0.0106 (9)
C310.0402 (13)0.0706 (16)0.0364 (12)0.0043 (12)0.0056 (10)0.0010 (11)
C320.0546 (17)0.109 (2)0.0678 (18)0.0135 (17)0.0090 (14)0.0293 (17)
C330.060 (2)0.183 (4)0.084 (2)0.036 (2)0.0046 (18)0.044 (3)
C340.0412 (18)0.220 (5)0.072 (2)0.003 (2)0.0046 (16)0.001 (3)
C350.0554 (19)0.147 (3)0.068 (2)0.031 (2)0.0091 (16)0.020 (2)
C360.0523 (16)0.0833 (19)0.0546 (15)0.0114 (14)0.0066 (12)0.0084 (14)
Geometric parameters (Å, º) top
C7—O71.216 (3)C16—H16A0.9700
C7—N11.364 (3)C16—H16B0.9700
C7—C11.494 (3)C17—C17A1.502 (3)
C1—C61.374 (3)C17—H17A0.9700
C1—C21.390 (3)C17—H17B0.9700
C2—C31.368 (3)C24—C251.529 (7)
C2—H20.9300C24—H24A0.9700
C3—F31.363 (3)C24—H24B0.9700
C3—C41.372 (4)C25—C261.517 (6)
C4—C51.370 (3)C25—H25A0.9700
C4—H40.9300C25—H25B0.9700
C5—C61.381 (3)C26—C271.532 (8)
C5—H50.9300C26—H26A0.9700
C6—H60.9300C26—H26B0.9700
N1—C121.380 (3)C27—H27A0.9700
N1—H10.8600C27—H27B0.9700
S11—C121.711 (2)C37—O371.241 (2)
S11—C17A1.731 (2)C37—C311.492 (3)
C12—C131.383 (3)C31—C321.377 (3)
C13—C13A1.450 (3)C31—C361.383 (3)
C13—C371.457 (3)C32—C331.380 (4)
C13A—C17A1.349 (3)C32—H320.9300
C13A—C141.505 (3)C33—C341.363 (5)
C14—C151.531 (5)C33—H330.9300
C14—H14A0.9700C34—C351.360 (5)
C14—H14B0.9700C34—H340.9300
C15—C161.517 (5)C35—C361.372 (4)
C15—H15A0.9700C35—H350.9300
C15—H15B0.9700C36—H360.9300
C16—C171.530 (7)
O7—C7—N1121.2 (2)C17—C16—H16B109.5
O7—C7—C1122.5 (2)H16A—C16—H16B108.0
N1—C7—C1116.4 (2)C17A—C17—C16109.6 (4)
C6—C1—C2119.1 (2)C17A—C17—H17A109.8
C6—C1—C7123.8 (2)C16—C17—H17A109.8
C2—C1—C7117.0 (2)C17A—C17—H17B109.8
C3—C2—C1118.2 (2)C16—C17—H17B109.8
C3—C2—H2120.9H17A—C17—H17B108.2
C1—C2—H2120.9C13A—C17A—C17125.7 (2)
F3—C3—C2118.0 (2)C13A—C17A—S11113.12 (17)
F3—C3—C4118.2 (2)C17—C17A—S11121.0 (2)
C2—C3—C4123.7 (2)C25—C24—H24A109.2
C5—C4—C3117.3 (2)C25—C24—H24B109.2
C5—C4—H4121.3H24A—C24—H24B107.9
C3—C4—H4121.3C26—C25—C24111.9 (8)
C4—C5—C6120.6 (2)C26—C25—H25A109.2
C4—C5—H5119.7C24—C25—H25A109.2
C6—C5—H5119.7C26—C25—H25B109.2
C1—C6—C5121.0 (2)C24—C25—H25B109.2
C1—C6—H6119.5H25A—C25—H25B107.9
C5—C6—H6119.5C25—C26—C27109.2 (9)
C7—N1—C12124.59 (19)C25—C26—H26A109.8
C7—N1—H1117.7C27—C26—H26A109.8
C12—N1—H1117.7C25—C26—H26B109.8
C12—S11—C17A90.94 (11)C27—C26—H26B109.8
N1—C12—C13124.67 (19)H26A—C26—H26B108.3
N1—C12—S11122.51 (17)C26—C27—H27A110.2
C13—C12—S11112.82 (16)C26—C27—H27B110.2
C12—C13—C13A111.11 (19)H27A—C27—H27B108.5
C12—C13—C37120.50 (18)O37—C37—C13121.6 (2)
C13A—C13—C37128.3 (2)O37—C37—C31116.7 (2)
C17A—C13A—C13112.0 (2)C13—C37—C31121.72 (19)
C17A—C13A—C14121.3 (2)C32—C31—C36118.8 (2)
C13—C13A—C14126.7 (2)C32—C31—C37119.4 (2)
C13A—C14—C15111.0 (3)C36—C31—C37121.6 (2)
C13A—C14—H14A109.4C31—C32—C33120.1 (3)
C15—C14—H14A109.4C31—C32—H32119.9
C13A—C14—H14B109.4C33—C32—H32119.9
C15—C14—H14B109.4C34—C33—C32119.9 (3)
H14A—C14—H14B108.0C34—C33—H33120.0
C16—C15—C14109.4 (4)C32—C33—H33120.0
C16—C15—H15A109.8C35—C34—C33120.7 (3)
C14—C15—H15A109.8C35—C34—H34119.6
C16—C15—H15B109.8C33—C34—H34119.6
C14—C15—H15B109.8C34—C35—C36119.7 (3)
H15A—C15—H15B108.2C34—C35—H35120.1
C15—C16—C17110.9 (5)C36—C35—H35120.1
C15—C16—H16A109.5C35—C36—C31120.6 (3)
C17—C16—H16A109.5C35—C36—H36119.7
C15—C16—H16B109.5C31—C36—H36119.7
O7—C7—C1—C6155.4 (2)C13—C13A—C14—C15157.6 (4)
N1—C7—C1—C624.6 (3)C13A—C14—C15—C1650.1 (9)
O7—C7—C1—C221.3 (3)C14—C15—C16—C1765.8 (9)
N1—C7—C1—C2158.70 (19)C15—C16—C17—C17A45.8 (10)
C6—C1—C2—C31.8 (3)C13—C13A—C17A—C17176.0 (6)
C7—C1—C2—C3178.6 (2)C14—C13A—C17A—C171.1 (9)
C1—C2—C3—F3179.54 (19)C13—C13A—C17A—S111.1 (2)
C1—C2—C3—C41.5 (4)C14—C13A—C17A—S11176.0 (5)
F3—C3—C4—C5179.1 (2)C16—C17—C17A—C13A14.3 (11)
C2—C3—C4—C50.1 (4)C16—C17—C17A—S11171.1 (4)
C3—C4—C5—C60.9 (4)C12—S11—C17A—C13A0.08 (18)
C2—C1—C6—C50.8 (3)C12—S11—C17A—C17175.1 (6)
C7—C1—C6—C5177.4 (2)C24—C25—C26—C2764.7 (15)
C4—C5—C6—C10.6 (4)C12—C13—C37—O3713.2 (3)
O7—C7—N1—C120.4 (3)C13A—C13—C37—O37164.1 (2)
C1—C7—N1—C12179.60 (18)C12—C13—C37—C31166.0 (2)
C7—N1—C12—C13179.27 (19)C13A—C13—C37—C3116.7 (3)
C7—N1—C12—S110.0 (3)O37—C37—C31—C3248.4 (3)
C17A—S11—C12—N1178.05 (17)C13—C37—C31—C32132.4 (2)
C17A—S11—C12—C131.32 (16)O37—C37—C31—C36125.9 (2)
N1—C12—C13—C13A177.20 (17)C13—C37—C31—C3653.4 (3)
S11—C12—C13—C13A2.2 (2)C36—C31—C32—C331.0 (4)
N1—C12—C13—C370.5 (3)C37—C31—C32—C33175.5 (3)
S11—C12—C13—C37179.90 (16)C31—C32—C33—C340.8 (5)
C12—C13—C13A—C17A2.1 (3)C32—C33—C34—C350.1 (6)
C37—C13—C13A—C17A179.6 (2)C33—C34—C35—C360.7 (5)
C12—C13—C13A—C14174.8 (5)C34—C35—C36—C310.5 (4)
C37—C13—C13A—C142.7 (6)C32—C31—C36—C350.4 (4)
C17A—C13A—C14—C1519.0 (9)C37—C31—C36—C35174.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O370.862.012.650 (3)130
N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-chlorobenzamide (II) top
Crystal data top
C22H18ClNO2SF(000) = 824
Mr = 395.88Dx = 1.362 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.6776 (6) ÅCell parameters from 3743 reflections
b = 14.2461 (8) Åθ = 2.3–25.9°
c = 12.2957 (7) ŵ = 0.32 mm1
β = 109.336 (2)°T = 296 K
V = 1930.13 (18) Å3Block, colourless
Z = 40.25 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2127 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.047
φ and ω scansθmax = 25.9°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1314
Tmin = 0.882, Tmax = 0.937k = 1717
28361 measured reflectionsl = 1415
3743 independent reflections
Refinement top
Refinement on F212 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0477P)2 + 1.4106P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3743 reflectionsΔρmax = 0.30 e Å3
257 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)
C70.3052 (3)0.1590 (2)0.3054 (3)0.0537 (8)
O70.32402 (18)0.07451 (16)0.3102 (2)0.0725 (7)
C10.1822 (2)0.1999 (2)0.2546 (2)0.0489 (7)
C20.0837 (3)0.1403 (2)0.2274 (3)0.0650 (9)
H20.09600.07630.24200.078*
C30.0329 (3)0.1740 (2)0.1790 (3)0.0677 (9)
H30.09880.13330.16130.081*
C40.0506 (3)0.2678 (2)0.1575 (3)0.0594 (8)
Cl40.19694 (8)0.31045 (8)0.09347 (9)0.0892 (4)
C50.0452 (3)0.3286 (2)0.1820 (3)0.0653 (9)
H50.03210.39240.16630.078*
C60.1611 (3)0.2943 (2)0.2301 (3)0.0623 (9)
H60.22650.33540.24660.075*
N10.39838 (19)0.22082 (17)0.3469 (2)0.0533 (6)
H10.37960.27930.34530.064*
S110.57075 (7)0.08612 (6)0.41343 (8)0.0635 (3)
C120.5191 (2)0.1988 (2)0.3909 (2)0.0490 (7)
C130.6120 (2)0.2646 (2)0.4221 (3)0.0494 (7)
C13A0.7289 (2)0.2195 (2)0.4669 (3)0.0508 (7)0.645 (7)
C140.8512 (4)0.2670 (4)0.512 (2)0.0704 (12)0.645 (7)
H14A0.84580.32150.55690.084*0.645 (7)
H14B0.87480.28830.44700.084*0.645 (7)
C150.9492 (4)0.1985 (4)0.5870 (6)0.073 (2)0.645 (7)
H15A1.02910.22580.60300.088*0.645 (7)
H15B0.93590.18810.65990.088*0.645 (7)
C160.9424 (5)0.1075 (5)0.5256 (8)0.098 (4)0.645 (7)
H16A1.00970.06780.56840.117*0.645 (7)
H16B0.94870.11870.45000.117*0.645 (7)
C170.8221 (5)0.0579 (3)0.513 (2)0.0762 (16)0.645 (7)
H17A0.81140.00510.46060.091*0.645 (7)
H17B0.82320.03410.58710.091*0.645 (7)
C17A0.7193 (3)0.1256 (2)0.4670 (3)0.0577 (8)0.645 (7)
C23A0.7289 (2)0.2195 (2)0.4669 (3)0.0508 (7)0.355 (7)
C240.8530 (6)0.2643 (5)0.517 (4)0.0704 (12)0.355 (7)
H24B0.86380.28720.59410.084*0.355 (7)
H24A0.85940.31730.46990.084*0.355 (7)
C250.9537 (7)0.1911 (8)0.5217 (11)0.073 (2)0.355 (7)
H25A0.95140.17610.44410.088*0.355 (7)
H25B1.03280.21740.56310.088*0.355 (7)
C260.9341 (8)0.1042 (9)0.5808 (13)0.098 (4)0.355 (7)
H26A0.92480.12010.65410.117*0.355 (7)
H26B1.00360.06280.59540.117*0.355 (7)
C270.8192 (8)0.0548 (5)0.503 (4)0.0762 (16)0.355 (7)
H27A0.83350.02870.43590.091*0.355 (7)
H27B0.79710.00390.54480.091*0.355 (7)
C27A0.7193 (3)0.1256 (2)0.4670 (3)0.0577 (8)0.355 (7)
C370.5843 (3)0.3642 (2)0.4080 (3)0.0572 (8)
O370.4800 (2)0.39474 (16)0.3860 (3)0.0874 (8)
C310.6826 (2)0.4328 (2)0.4160 (3)0.0512 (7)
C320.7229 (3)0.4937 (3)0.5060 (3)0.0753 (10)
H320.68870.49340.56440.090*
C330.8159 (4)0.5564 (3)0.5100 (5)0.1018 (15)
H330.84550.59690.57240.122*
C340.8628 (4)0.5585 (3)0.4238 (5)0.0999 (15)
H340.92370.60130.42610.120*
C350.8222 (4)0.4993 (4)0.3349 (4)0.1031 (15)
H350.85500.50110.27560.124*
C360.7326 (3)0.4361 (3)0.3309 (3)0.0810 (11)
H360.70560.39480.26900.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C70.0484 (17)0.058 (2)0.0569 (19)0.0049 (15)0.0201 (14)0.0003 (15)
O70.0522 (13)0.0532 (15)0.1014 (18)0.0018 (10)0.0109 (12)0.0012 (12)
C10.0429 (16)0.0499 (18)0.0536 (17)0.0011 (13)0.0156 (13)0.0025 (14)
C20.0530 (19)0.057 (2)0.079 (2)0.0055 (15)0.0133 (16)0.0044 (17)
C30.0455 (18)0.068 (2)0.082 (2)0.0083 (16)0.0109 (16)0.0026 (19)
C40.0462 (17)0.073 (2)0.0562 (19)0.0082 (16)0.0132 (14)0.0036 (17)
Cl40.0557 (5)0.1037 (8)0.0976 (7)0.0217 (5)0.0110 (5)0.0074 (6)
C50.057 (2)0.060 (2)0.075 (2)0.0078 (16)0.0181 (17)0.0029 (17)
C60.0493 (18)0.057 (2)0.077 (2)0.0060 (15)0.0171 (16)0.0007 (17)
N10.0385 (13)0.0463 (14)0.0746 (17)0.0016 (11)0.0180 (12)0.0005 (12)
S110.0506 (5)0.0498 (5)0.0864 (6)0.0004 (4)0.0176 (4)0.0018 (4)
C120.0434 (15)0.0482 (17)0.0576 (18)0.0018 (13)0.0198 (13)0.0001 (14)
C130.0435 (15)0.0469 (17)0.0601 (18)0.0009 (13)0.0204 (13)0.0003 (14)
C13A0.0399 (15)0.0500 (19)0.0626 (19)0.0030 (13)0.0171 (13)0.0024 (14)
C140.0395 (16)0.063 (2)0.100 (3)0.0026 (15)0.0122 (17)0.005 (2)
C150.042 (2)0.075 (3)0.093 (6)0.005 (2)0.009 (3)0.008 (4)
C160.058 (3)0.083 (3)0.124 (9)0.028 (2)0.007 (4)0.031 (5)
C170.056 (2)0.065 (2)0.097 (4)0.0137 (17)0.011 (2)0.004 (2)
C17A0.0476 (17)0.056 (2)0.068 (2)0.0058 (14)0.0169 (15)0.0026 (16)
C23A0.0399 (15)0.0500 (19)0.0626 (19)0.0030 (13)0.0171 (13)0.0024 (14)
C240.0395 (16)0.063 (2)0.100 (3)0.0026 (15)0.0122 (17)0.005 (2)
C250.042 (2)0.075 (3)0.093 (6)0.005 (2)0.009 (3)0.008 (4)
C260.058 (3)0.083 (3)0.124 (9)0.028 (2)0.007 (4)0.031 (5)
C270.056 (2)0.065 (2)0.097 (4)0.0137 (17)0.011 (2)0.004 (2)
C27A0.0476 (17)0.056 (2)0.068 (2)0.0058 (14)0.0169 (15)0.0026 (16)
C370.0455 (17)0.0541 (19)0.071 (2)0.0009 (14)0.0181 (15)0.0027 (16)
O370.0502 (13)0.0564 (14)0.155 (2)0.0055 (11)0.0335 (14)0.0010 (15)
C310.0432 (16)0.0512 (19)0.0553 (18)0.0026 (13)0.0110 (14)0.0002 (15)
C320.067 (2)0.083 (3)0.072 (2)0.004 (2)0.0176 (18)0.014 (2)
C330.082 (3)0.077 (3)0.122 (4)0.011 (2)0.002 (3)0.040 (3)
C340.061 (3)0.073 (3)0.154 (5)0.014 (2)0.020 (3)0.013 (3)
C350.074 (3)0.133 (4)0.105 (3)0.025 (3)0.032 (2)0.024 (3)
C360.062 (2)0.116 (3)0.067 (2)0.022 (2)0.0238 (19)0.009 (2)
Geometric parameters (Å, º) top
C7—O71.222 (3)C16—H16A0.9700
C7—N11.361 (4)C16—H16B0.9700
C7—C11.483 (4)C17—C17A1.497 (5)
C1—C21.380 (4)C17—H17A0.9700
C1—C61.382 (4)C17—H17B0.9700
C2—C31.379 (4)C24—C251.557 (11)
C2—H20.9300C24—H24B0.9700
C3—C41.364 (4)C24—H24A0.9700
C3—H30.9300C25—C261.491 (8)
C4—C51.367 (4)C25—H25A0.9700
C4—Cl41.738 (3)C25—H25B0.9700
C5—C61.375 (4)C26—C271.537 (12)
C5—H50.9300C26—H26A0.9700
C6—H60.9300C26—H26B0.9700
N1—C121.369 (3)C27—H27A0.9700
N1—H10.8600C27—H27B0.9700
S11—C121.705 (3)C37—O371.235 (3)
S11—C17A1.732 (3)C37—C311.487 (4)
C12—C131.388 (4)C31—C361.357 (4)
C13—C13A1.444 (4)C31—C321.362 (4)
C13—C371.452 (4)C32—C331.394 (6)
C13A—C17A1.343 (4)C32—H320.9300
C13A—C141.511 (4)C33—C341.345 (6)
C14—C151.556 (11)C33—H330.9300
C14—H14A0.9700C34—C351.337 (6)
C14—H14B0.9700C34—H340.9300
C15—C161.489 (8)C35—C361.369 (5)
C15—H15A0.9700C35—H350.9300
C15—H15B0.9700C36—H360.9300
C16—C171.534 (11)
O7—C7—N1120.7 (3)C17—C16—H16B109.6
O7—C7—C1122.8 (3)H16A—C16—H16B108.1
N1—C7—C1116.5 (3)C17A—C17—C16109.5 (6)
C2—C1—C6118.2 (3)C17A—C17—H17A109.8
C2—C1—C7118.3 (3)C16—C17—H17A109.8
C6—C1—C7123.5 (3)C17A—C17—H17B109.8
C3—C2—C1121.0 (3)C16—C17—H17B109.8
C3—C2—H2119.5H17A—C17—H17B108.2
C1—C2—H2119.5C13A—C17A—C17125.8 (3)
C4—C3—C2119.3 (3)C13A—C17A—S11113.4 (2)
C4—C3—H3120.3C17—C17A—S11120.8 (3)
C2—C3—H3120.3C25—C24—H24B109.7
C3—C4—C5121.2 (3)C25—C24—H24A109.7
C3—C4—Cl4119.5 (3)H24B—C24—H24A108.2
C5—C4—Cl4119.2 (3)C26—C25—C24109.8 (11)
C4—C5—C6119.1 (3)C26—C25—H25A109.7
C4—C5—H5120.5C24—C25—H25A109.7
C6—C5—H5120.5C26—C25—H25B109.7
C5—C6—C1121.3 (3)C24—C25—H25B109.7
C5—C6—H6119.4H25A—C25—H25B108.2
C1—C6—H6119.4C25—C26—C27108.7 (12)
C7—N1—C12126.3 (3)C25—C26—H26A109.9
C7—N1—H1116.9C27—C26—H26A109.9
C12—N1—H1116.9C25—C26—H26B109.9
C12—S11—C17A90.68 (14)C27—C26—H26B109.9
N1—C12—C13124.2 (3)H26A—C26—H26B108.3
N1—C12—S11122.8 (2)C26—C27—H27A110.1
C13—C12—S11112.9 (2)C26—C27—H27B110.1
C12—C13—C13A111.0 (3)H27A—C27—H27B108.4
C12—C13—C37120.3 (2)O37—C37—C13122.3 (3)
C13A—C13—C37128.8 (3)O37—C37—C31117.8 (3)
C17A—C13A—C13112.1 (3)C13—C37—C31119.8 (2)
C17A—C13A—C14121.1 (3)C36—C31—C32118.9 (3)
C13—C13A—C14126.9 (3)C36—C31—C37119.5 (3)
C13A—C14—C15110.8 (6)C32—C31—C37121.5 (3)
C13A—C14—H14A109.5C31—C32—C33119.5 (4)
C15—C14—H14A109.5C31—C32—H32120.3
C13A—C14—H14B109.5C33—C32—H32120.3
C15—C14—H14B109.5C34—C33—C32120.2 (4)
H14A—C14—H14B108.1C34—C33—H33119.9
C16—C15—C14109.8 (9)C32—C33—H33119.9
C16—C15—H15A109.7C35—C34—C33120.2 (4)
C14—C15—H15A109.7C35—C34—H34119.9
C16—C15—H15B109.7C33—C34—H34119.9
C14—C15—H15B109.7C34—C35—C36120.3 (4)
H15A—C15—H15B108.2C34—C35—H35119.9
C15—C16—C17110.3 (10)C36—C35—H35119.9
C15—C16—H16A109.6C31—C36—C35120.9 (4)
C17—C16—H16A109.6C31—C36—H36119.5
C15—C16—H16B109.6C35—C36—H36119.5
O7—C7—C1—C29.9 (5)C13—C13A—C14—C15161.7 (8)
N1—C7—C1—C2170.5 (3)C13A—C14—C15—C1649 (2)
O7—C7—C1—C6168.4 (3)C14—C15—C16—C1766.2 (18)
N1—C7—C1—C611.3 (4)C15—C16—C17—C17A49 (2)
C6—C1—C2—C31.1 (5)C13—C13A—C17A—C17176.9 (14)
C7—C1—C2—C3179.4 (3)C14—C13A—C17A—C172 (2)
C1—C2—C3—C40.2 (5)C13—C13A—C17A—S110.1 (4)
C2—C3—C4—C50.6 (5)C14—C13A—C17A—S11179.4 (13)
C2—C3—C4—Cl4178.5 (3)C16—C17—C17A—C13A17 (2)
C3—C4—C5—C60.6 (5)C16—C17—C17A—S11165.8 (10)
Cl4—C4—C5—C6178.5 (2)C12—S11—C17A—C13A0.4 (3)
C4—C5—C6—C10.4 (5)C12—S11—C17A—C17176.8 (13)
C2—C1—C6—C51.1 (5)C24—C25—C26—C2769.1 (18)
C7—C1—C6—C5179.4 (3)C12—C13—C37—O3711.6 (5)
O7—C7—N1—C123.7 (5)C13A—C13—C37—O37168.1 (3)
C1—C7—N1—C12175.9 (3)C12—C13—C37—C31166.2 (3)
C7—N1—C12—C13173.6 (3)C13A—C13—C37—C3114.2 (5)
C7—N1—C12—S116.6 (4)O37—C37—C31—C36107.6 (4)
C17A—S11—C12—N1179.3 (3)C13—C37—C31—C3670.2 (4)
C17A—S11—C12—C130.6 (2)O37—C37—C31—C3271.4 (4)
N1—C12—C13—C13A179.2 (3)C13—C37—C31—C32110.7 (4)
S11—C12—C13—C13A0.6 (3)C36—C31—C32—C331.3 (5)
N1—C12—C13—C370.5 (5)C37—C31—C32—C33179.6 (3)
S11—C12—C13—C37179.7 (2)C31—C32—C33—C341.9 (6)
C12—C13—C13A—C17A0.3 (4)C32—C33—C34—C351.3 (7)
C37—C13—C13A—C17A180.0 (3)C33—C34—C35—C360.0 (7)
C12—C13—C13A—C14179.0 (14)C32—C31—C36—C350.1 (5)
C37—C13—C13A—C140.7 (14)C37—C31—C36—C35179.1 (3)
C17A—C13A—C14—C1517 (2)C34—C35—C36—C310.6 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O370.861.992.641 (3)132
C3—H3···Cg1i0.932.763.676 (4)169
C14—H14A···Cg10.972.963.475 (9)114
C24—H24A···Cg10.972.733.530 (17)140
Symmetry code: (i) x+1/2, y1/2, z+1/2.
N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-difluorobenzamide (III) top
Crystal data top
C22H17F2NO2SZ = 2
Mr = 397.43F(000) = 412
Triclinic, P1Dx = 1.383 Mg m3
a = 7.6718 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.8833 (3) ÅCell parameters from 4414 reflections
c = 13.5925 (5) Åθ = 1.6–27.6°
α = 104.925 (4)°µ = 0.21 mm1
β = 95.476 (2)°T = 296 K
γ = 103.633 (3)°Block, colourless
V = 954.32 (6) Å30.20 × 0.20 × 0.15 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2814 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.041
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 99
Tmin = 0.942, Tmax = 0.970k = 1212
21940 measured reflectionsl = 1717
4375 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0379P)2 + 0.3345P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.108(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.23 e Å3
4375 reflectionsΔρmin = 0.25 e Å3
267 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
12 restraintsExtinction coefficient: 0.0131 (17)
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)
C70.2985 (3)0.1093 (2)0.25624 (16)0.0428 (5)
O70.3232 (2)0.18513 (16)0.17654 (11)0.0596 (4)
C10.3154 (3)0.1458 (2)0.35650 (15)0.0413 (5)
C20.4588 (3)0.1956 (2)0.38729 (17)0.0513 (5)
F20.5870 (2)0.20460 (18)0.32721 (11)0.0828 (5)
C30.4795 (4)0.2323 (2)0.47761 (19)0.0631 (7)
H30.57790.26610.49530.076*
C40.3530 (4)0.2184 (2)0.54089 (18)0.0645 (7)
H40.36570.24260.60240.077*
C50.2073 (4)0.1690 (3)0.51490 (18)0.0620 (6)
H50.12120.15910.55810.074*
C60.1921 (3)0.1348 (2)0.42373 (17)0.0513 (5)
F60.04692 (19)0.08836 (18)0.39741 (12)0.0821 (5)
N10.2570 (2)0.01864 (17)0.26251 (12)0.0430 (4)
H10.24180.06680.32200.052*
S110.28668 (7)0.00737 (6)0.06263 (4)0.04521 (16)
C120.2370 (2)0.0786 (2)0.18196 (14)0.0376 (4)
C130.1764 (3)0.2008 (2)0.18835 (14)0.0384 (4)
C13A0.1798 (3)0.2408 (2)0.09357 (15)0.0408 (5)0.784 (6)
C140.1373 (9)0.3748 (4)0.0747 (3)0.0538 (13)0.784 (6)
H14A0.17860.45560.13730.065*0.784 (6)
H14B0.00690.35670.05600.065*0.784 (6)
C150.2319 (6)0.4131 (4)0.0120 (3)0.0719 (13)0.784 (6)
H15A0.19230.49110.03010.086*0.784 (6)
H15B0.36240.44670.01110.086*0.784 (6)
C160.1877 (6)0.2814 (4)0.1058 (3)0.0721 (12)0.784 (6)
H16A0.23780.30970.16260.087*0.784 (6)
H16B0.05670.24490.12620.087*0.784 (6)
C170.2639 (16)0.1612 (6)0.0845 (3)0.0596 (8)0.784 (6)
H17B0.20360.06980.13650.071*0.784 (6)
H17A0.39280.18330.08810.071*0.784 (6)
C17A0.2358 (3)0.1471 (2)0.02047 (15)0.0430 (5)0.784 (6)
C23A0.1798 (3)0.2408 (2)0.09357 (15)0.0408 (5)0.216 (6)
C240.178 (4)0.3878 (13)0.0789 (10)0.0538 (13)0.216 (6)
H24A0.29170.45900.11400.065*0.216 (6)
H24B0.07980.41970.10910.065*0.216 (6)
C250.1530 (18)0.3780 (16)0.0355 (10)0.0719 (13)0.216 (6)
H25A0.03030.32090.06780.086*0.216 (6)
H25B0.16850.47490.04310.086*0.216 (6)
C260.2875 (19)0.3092 (14)0.0896 (10)0.0721 (12)0.216 (6)
H26A0.41040.36370.05580.087*0.216 (6)
H26B0.27480.31220.16060.087*0.216 (6)
C270.255 (6)0.152 (2)0.0873 (11)0.0596 (8)0.216 (6)
H27A0.14480.09200.13460.071*0.216 (6)
H27B0.35580.11500.10840.071*0.216 (6)
C27A0.2358 (3)0.1471 (2)0.02047 (15)0.0430 (5)0.216 (6)
C370.1167 (3)0.2722 (2)0.28286 (15)0.0421 (5)
O370.1794 (2)0.26502 (18)0.36795 (11)0.0648 (5)
C310.0315 (3)0.34488 (19)0.27706 (14)0.0371 (4)
C320.0286 (3)0.4664 (2)0.35635 (16)0.0496 (5)
H320.07020.50620.40980.060*
C330.1713 (3)0.5282 (2)0.35617 (19)0.0594 (6)
H330.16800.61060.40900.071*
C340.3193 (3)0.4684 (2)0.27803 (19)0.0564 (6)
H340.41590.51030.27840.068*
C350.3245 (3)0.3475 (2)0.19989 (17)0.0506 (5)
H350.42520.30660.14760.061*
C360.1803 (3)0.2864 (2)0.19885 (15)0.0436 (5)
H360.18330.20520.14510.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C70.0445 (12)0.0452 (11)0.0463 (12)0.0214 (9)0.0107 (9)0.0168 (9)
O70.0837 (12)0.0613 (9)0.0483 (9)0.0418 (9)0.0203 (8)0.0172 (7)
C10.0490 (12)0.0376 (10)0.0434 (11)0.0190 (9)0.0079 (9)0.0157 (9)
C20.0582 (14)0.0505 (12)0.0540 (13)0.0283 (11)0.0099 (11)0.0175 (10)
F20.0810 (10)0.1194 (12)0.0805 (10)0.0712 (10)0.0281 (8)0.0394 (9)
C30.0720 (17)0.0602 (14)0.0618 (15)0.0279 (13)0.0077 (13)0.0234 (12)
C40.0820 (19)0.0572 (14)0.0531 (14)0.0079 (13)0.0050 (13)0.0299 (12)
C50.0734 (17)0.0640 (15)0.0552 (14)0.0138 (13)0.0207 (12)0.0295 (12)
C60.0539 (13)0.0525 (12)0.0583 (14)0.0219 (11)0.0134 (11)0.0263 (11)
F60.0696 (10)0.1271 (13)0.0931 (11)0.0595 (9)0.0414 (8)0.0669 (10)
N10.0573 (11)0.0476 (9)0.0354 (9)0.0285 (8)0.0115 (8)0.0170 (7)
S110.0528 (3)0.0506 (3)0.0391 (3)0.0232 (2)0.0131 (2)0.0146 (2)
C120.0373 (11)0.0435 (10)0.0367 (10)0.0169 (9)0.0073 (8)0.0141 (8)
C130.0380 (11)0.0447 (10)0.0382 (10)0.0184 (9)0.0061 (8)0.0149 (8)
C13A0.0361 (11)0.0501 (11)0.0436 (11)0.0159 (9)0.0073 (9)0.0219 (9)
C140.055 (3)0.0614 (15)0.0632 (15)0.0265 (17)0.0151 (16)0.0373 (13)
C150.065 (3)0.084 (3)0.105 (3)0.036 (2)0.044 (2)0.068 (2)
C160.073 (3)0.104 (3)0.064 (2)0.032 (3)0.022 (2)0.056 (2)
C170.0620 (18)0.0813 (19)0.0489 (13)0.0252 (15)0.0207 (12)0.0327 (13)
C17A0.0385 (11)0.0563 (12)0.0405 (11)0.0157 (9)0.0079 (9)0.0219 (10)
C23A0.0361 (11)0.0501 (11)0.0436 (11)0.0159 (9)0.0073 (9)0.0219 (9)
C240.055 (3)0.0614 (15)0.0632 (15)0.0265 (17)0.0151 (16)0.0373 (13)
C250.065 (3)0.084 (3)0.105 (3)0.036 (2)0.044 (2)0.068 (2)
C260.073 (3)0.104 (3)0.064 (2)0.032 (3)0.022 (2)0.056 (2)
C270.0620 (18)0.0813 (19)0.0489 (13)0.0252 (15)0.0207 (12)0.0327 (13)
C27A0.0385 (11)0.0563 (12)0.0405 (11)0.0157 (9)0.0079 (9)0.0219 (10)
C370.0500 (12)0.0421 (10)0.0392 (11)0.0202 (9)0.0072 (9)0.0134 (9)
O370.0888 (12)0.0849 (11)0.0370 (8)0.0588 (10)0.0047 (8)0.0159 (8)
C310.0431 (11)0.0380 (10)0.0362 (10)0.0169 (9)0.0086 (9)0.0152 (8)
C320.0544 (13)0.0453 (11)0.0471 (12)0.0201 (10)0.0033 (10)0.0059 (9)
C330.0646 (15)0.0453 (12)0.0690 (16)0.0276 (11)0.0132 (13)0.0052 (11)
C340.0506 (14)0.0554 (13)0.0777 (17)0.0304 (11)0.0192 (12)0.0267 (12)
C350.0402 (12)0.0583 (13)0.0568 (13)0.0155 (10)0.0026 (10)0.0226 (11)
C360.0492 (12)0.0427 (11)0.0394 (11)0.0169 (9)0.0060 (9)0.0093 (9)
Geometric parameters (Å, º) top
C7—O71.208 (2)C16—H16A0.9700
C7—N11.359 (2)C16—H16B0.9700
C7—C11.499 (3)C17—C17A1.499 (3)
C1—C21.379 (3)C17—H17B0.9700
C1—C61.380 (3)C17—H17A0.9700
C2—F21.341 (2)C24—C251.522 (6)
C2—C31.373 (3)C24—H24A0.9700
C3—C41.365 (3)C24—H24B0.9700
C3—H30.9300C25—C261.512 (6)
C4—C51.372 (3)C25—H25A0.9700
C4—H40.9300C25—H25B0.9700
C5—C61.368 (3)C26—C271.523 (7)
C5—H50.9300C26—H26A0.9700
C6—F61.353 (2)C26—H26B0.9700
N1—C121.385 (2)C27—H27A0.9700
N1—H10.8600C27—H27B0.9700
S11—C121.7111 (19)C37—O371.236 (2)
S11—C17A1.7338 (19)C37—C311.487 (3)
C12—C131.379 (2)C31—C361.381 (3)
C13—C13A1.443 (3)C31—C321.386 (3)
C13—C371.468 (3)C32—C331.374 (3)
C13A—C17A1.351 (3)C32—H320.9300
C13A—C141.513 (3)C33—C341.377 (3)
C14—C151.525 (4)C33—H330.9300
C14—H14A0.9700C34—C351.369 (3)
C14—H14B0.9700C34—H340.9300
C15—C161.513 (4)C35—C361.379 (3)
C15—H15A0.9700C35—H350.9300
C15—H15B0.9700C36—H360.9300
C16—C171.520 (6)
O7—C7—N1122.35 (18)C17—C16—H16B109.3
O7—C7—C1123.19 (17)H16A—C16—H16B107.9
N1—C7—C1114.45 (17)C17A—C17—C16110.1 (3)
C2—C1—C6114.98 (18)C17A—C17—H17B109.6
C2—C1—C7120.96 (18)C16—C17—H17B109.6
C6—C1—C7124.06 (18)C17A—C17—H17A109.6
F2—C2—C3118.5 (2)C16—C17—H17A109.6
F2—C2—C1118.20 (18)H17B—C17—H17A108.1
C3—C2—C1123.3 (2)C13A—C17A—C17125.9 (2)
C4—C3—C2118.7 (2)C13A—C17A—S11112.59 (14)
C4—C3—H3120.6C17—C17A—S11121.4 (2)
C2—C3—H3120.6C25—C24—H24A109.6
C3—C4—C5120.9 (2)C25—C24—H24B109.6
C3—C4—H4119.6H24A—C24—H24B108.1
C5—C4—H4119.6C26—C25—C24111.7 (7)
C6—C5—C4118.1 (2)C26—C25—H25A109.3
C6—C5—H5120.9C24—C25—H25A109.3
C4—C5—H5120.9C26—C25—H25B109.3
F6—C6—C5118.1 (2)C24—C25—H25B109.3
F6—C6—C1117.93 (18)H25A—C25—H25B107.9
C5—C6—C1124.0 (2)C25—C26—C27110.3 (8)
C7—N1—C12126.00 (16)C25—C26—H26A109.6
C7—N1—H1117.0C27—C26—H26A109.6
C12—N1—H1117.0C25—C26—H26B109.6
C12—S11—C17A91.04 (9)C27—C26—H26B109.6
C13—C12—N1124.46 (17)H26A—C26—H26B108.1
C13—C12—S11112.65 (14)C26—C27—H27A110.0
N1—C12—S11122.90 (13)C26—C27—H27B110.0
C12—C13—C13A111.36 (16)H27A—C27—H27B108.4
C12—C13—C37120.60 (16)O37—C37—C13120.90 (17)
C13A—C13—C37128.04 (16)O37—C37—C31118.50 (17)
C17A—C13A—C13112.28 (16)C13—C37—C31120.43 (16)
C17A—C13A—C14121.3 (2)C36—C31—C32119.09 (18)
C13—C13A—C14126.4 (2)C36—C31—C37121.26 (17)
C13A—C14—C15109.7 (3)C32—C31—C37119.41 (17)
C13A—C14—H14A109.7C33—C32—C31120.2 (2)
C15—C14—H14A109.7C33—C32—H32119.9
C13A—C14—H14B109.7C31—C32—H32119.9
C15—C14—H14B109.7C32—C33—C34120.2 (2)
H14A—C14—H14B108.2C32—C33—H33119.9
C16—C15—C14110.2 (4)C34—C33—H33119.9
C16—C15—H15A109.6C35—C34—C33120.1 (2)
C14—C15—H15A109.6C35—C34—H34119.9
C16—C15—H15B109.6C33—C34—H34119.9
C14—C15—H15B109.6C34—C35—C36119.9 (2)
H15A—C15—H15B108.1C34—C35—H35120.1
C15—C16—C17111.7 (4)C36—C35—H35120.1
C15—C16—H16A109.3C35—C36—C31120.51 (19)
C17—C16—H16A109.3C35—C36—H36119.7
C15—C16—H16B109.3C31—C36—H36119.7
O7—C7—C1—C244.1 (3)C37—C13—C13A—C145.8 (4)
N1—C7—C1—C2134.5 (2)C17A—C13A—C14—C1521.2 (6)
O7—C7—C1—C6135.1 (2)C13—C13A—C14—C15155.4 (3)
N1—C7—C1—C646.3 (3)C13A—C14—C15—C1652.0 (6)
C6—C1—C2—F2177.94 (19)C14—C15—C16—C1765.0 (8)
C7—C1—C2—F22.8 (3)C15—C16—C17—C17A41.7 (10)
C6—C1—C2—C30.2 (3)C13—C13A—C17A—C17176.6 (6)
C7—C1—C2—C3179.1 (2)C14—C13A—C17A—C170.4 (8)
F2—C2—C3—C4177.7 (2)C13—C13A—C17A—S110.1 (2)
C1—C2—C3—C40.4 (4)C14—C13A—C17A—S11177.0 (3)
C2—C3—C4—C50.2 (4)C16—C17—C17A—C13A10.4 (11)
C3—C4—C5—C60.2 (4)C16—C17—C17A—S11173.3 (4)
C4—C5—C6—F6179.0 (2)C12—S11—C17A—C13A1.37 (16)
C4—C5—C6—C10.5 (4)C12—S11—C17A—C17175.4 (6)
C2—C1—C6—F6179.17 (19)C24—C25—C26—C2764.1 (14)
C7—C1—C6—F60.1 (3)C12—C13—C37—O3728.0 (3)
C2—C1—C6—C50.3 (3)C13A—C13—C37—O37152.8 (2)
C7—C1—C6—C5179.6 (2)C12—C13—C37—C31147.08 (19)
O7—C7—N1—C120.2 (3)C13A—C13—C37—C3132.1 (3)
C1—C7—N1—C12178.76 (18)O37—C37—C31—C36137.2 (2)
C7—N1—C12—C13172.90 (19)C13—C37—C31—C3638.0 (3)
C7—N1—C12—S117.3 (3)O37—C37—C31—C3237.0 (3)
C17A—S11—C12—C132.51 (16)C13—C37—C31—C32147.78 (19)
C17A—S11—C12—N1177.29 (17)C36—C31—C32—C330.7 (3)
N1—C12—C13—C13A176.82 (18)C37—C31—C32—C33175.0 (2)
S11—C12—C13—C13A3.0 (2)C31—C32—C33—C341.0 (3)
N1—C12—C13—C373.9 (3)C32—C33—C34—C350.3 (4)
S11—C12—C13—C37176.34 (15)C33—C34—C35—C360.7 (3)
C12—C13—C13A—C17A1.9 (2)C34—C35—C36—C311.0 (3)
C37—C13—C13A—C17A177.31 (19)C32—C31—C36—C350.4 (3)
C12—C13—C13A—C14174.9 (4)C37—C31—C36—C35173.88 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O370.862.082.718 (2)130
C3—H3···O37i0.932.503.326 (3)148
C17—H17A···O7ii0.972.593.494 (12)156
C4—H4···Cg1iii0.932.853.635 (2)143
C35—H35···Cg2iv0.932.753.520 (2)141
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z; (iii) x, y, z+1; (iv) x1, y, z.
N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2-methoxybenzamide (IV) top
Crystal data top
C23H21NO3SZ = 4
Mr = 391.47F(000) = 824
Triclinic, P1Dx = 1.344 Mg m3
a = 8.5129 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.9230 (14) ÅCell parameters from 8692 reflections
c = 19.031 (2) Åθ = 1.1–27.4°
α = 96.811 (5)°µ = 0.19 mm1
β = 102.665 (6)°T = 296 K
γ = 105.321 (5)°Block, colourless
V = 1935.1 (4) Å30.20 × 0.15 × 0.15 mm
Data collection top
Bruker Kappa APEXII
diffractometer
4159 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.072
φ and ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1010
Tmin = 0.935, Tmax = 0.972k = 1616
37373 measured reflectionsl = 2323
8015 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0707P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
8015 reflectionsΔρmax = 0.23 e Å3
511 parametersΔρmin = 0.36 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*/Ueq
C170.7291 (3)0.4920 (2)0.42332 (17)0.0432 (7)
O170.6890 (2)0.46367 (16)0.35654 (11)0.0583 (6)
C110.8727 (3)0.5902 (2)0.46126 (16)0.0415 (7)
C120.9407 (3)0.6250 (2)0.53685 (16)0.0445 (7)
C131.0831 (4)0.7148 (3)0.56369 (19)0.0558 (8)
H131.135 (4)0.735 (2)0.6153 (16)0.067*
C141.1547 (4)0.7718 (2)0.5164 (2)0.0623 (9)
H141.24940.83250.53500.075*
C151.0888 (4)0.7406 (3)0.4423 (2)0.0616 (9)
H151.13720.77990.41060.074*
C160.9503 (4)0.6504 (2)0.41536 (17)0.0520 (8)
H160.90660.62870.36490.062*
O120.8629 (2)0.56645 (16)0.58071 (11)0.0574 (5)
C180.9289 (4)0.5935 (3)0.65822 (16)0.0706 (10)
H18A1.04360.59170.67080.106*
H18B0.86240.54170.68050.106*
H18C0.92530.66550.67570.106*
N110.6436 (3)0.43260 (17)0.46496 (14)0.0420 (6)
H110.67260.45630.51150.071 (11)*
S1110.44061 (9)0.28363 (6)0.34524 (4)0.0479 (2)
C1120.5132 (3)0.3366 (2)0.43732 (14)0.0376 (6)
C1130.4327 (3)0.2715 (2)0.47888 (14)0.0349 (6)
C13A0.3002 (3)0.1774 (2)0.43310 (14)0.0366 (6)
C1140.1737 (3)0.0934 (2)0.45662 (15)0.0465 (7)
H11A0.13510.12930.49420.056*
H11B0.22780.04290.47780.056*
C1150.0235 (4)0.0303 (3)0.39350 (16)0.0585 (8)
H11C0.03950.03400.40810.070*
H11D0.05010.07540.38250.070*
C1160.0732 (4)0.0040 (2)0.32617 (17)0.0617 (9)
H11E0.02710.04670.28820.074*
H11F0.14520.05020.33680.074*
C1170.1663 (4)0.0936 (2)0.29797 (16)0.0556 (8)
H11G0.22360.06940.26340.067*
H11H0.08620.12690.27280.067*
C17A0.2920 (3)0.1753 (2)0.36089 (15)0.0421 (7)
C1370.4843 (3)0.2989 (2)0.55881 (15)0.0394 (7)
O1370.5584 (3)0.39291 (16)0.59155 (11)0.0584 (6)
C1310.4570 (3)0.2123 (2)0.60386 (14)0.0384 (6)
C1320.4077 (3)0.2322 (2)0.66724 (15)0.0493 (7)
H1320.38250.29680.67910.059*
C1330.3958 (4)0.1579 (3)0.71268 (17)0.0661 (9)
H1330.36080.17170.75490.079*
C1340.4347 (4)0.0635 (3)0.69670 (19)0.0676 (10)
H1340.42700.01360.72810.081*
C1350.4853 (3)0.0422 (2)0.6344 (2)0.0596 (9)
H1350.51340.02160.62380.072*
C1360.4944 (3)0.1162 (2)0.58719 (16)0.0480 (7)
H1360.52580.10100.54420.058*
C270.6652 (3)0.0187 (2)0.90359 (16)0.0422 (7)
O270.6146 (2)0.01895 (17)0.83797 (11)0.0642 (6)
C210.5718 (3)0.1027 (2)0.93938 (16)0.0414 (7)
C220.6084 (3)0.1044 (2)1.01425 (17)0.0446 (7)
C230.5056 (4)0.1841 (3)1.04075 (19)0.0615 (9)
H230.52930.18471.09080.074*
C240.3689 (4)0.2621 (3)0.9936 (2)0.0708 (10)
H240.30130.31561.01190.085*
C250.3312 (4)0.2623 (3)0.9203 (2)0.0709 (10)
H250.23800.31530.88870.085*
C260.4318 (4)0.1833 (2)0.89307 (18)0.0584 (8)
H260.40590.18380.84290.070*
O220.7458 (2)0.02601 (16)1.05790 (11)0.0558 (5)
C280.7914 (4)0.0238 (3)1.13475 (16)0.0661 (9)
H28A0.70280.01211.15530.099*
H28B0.89370.03441.15730.099*
H28C0.80850.09211.14350.099*
N210.8057 (3)0.05953 (16)0.94501 (12)0.0395 (5)
H210.83770.05670.99070.047*
S2110.85579 (9)0.15549 (6)0.82917 (4)0.0450 (2)
C2120.9009 (3)0.1431 (2)0.91981 (14)0.0361 (6)
C2131.0392 (3)0.2265 (2)0.96251 (14)0.0345 (6)
C23A1.1148 (3)0.2983 (2)0.91849 (14)0.0365 (6)
C2141.2753 (3)0.3921 (2)0.94344 (15)0.0485 (7)
H21A1.35730.37300.97950.058*
H21B1.25250.45560.96670.058*
C2151.3484 (4)0.4203 (3)0.87987 (17)0.0628 (9)
H21C1.43840.48900.89580.075*
H21D1.39630.36410.86420.075*
C2161.2157 (4)0.4297 (3)0.81655 (17)0.0649 (9)
H21E1.26780.45290.77830.078*
H21F1.16690.48520.83260.078*
C2171.0772 (4)0.3228 (2)0.78561 (16)0.0523 (8)
H21G0.97900.33630.75590.063*
H21H1.11540.27520.75440.063*
C27A1.0301 (3)0.2683 (2)0.84655 (15)0.0419 (7)
C2371.0898 (3)0.2345 (2)1.04255 (15)0.0387 (6)
O2371.0632 (2)0.15246 (15)1.07003 (10)0.0558 (5)
C2311.1630 (3)0.3431 (2)1.09194 (14)0.0362 (6)
C2321.2766 (3)0.3540 (2)1.15913 (15)0.0450 (7)
H2321.31260.29491.17110.054*
C2331.3360 (4)0.4516 (3)1.20796 (16)0.0550 (8)
H2331.41310.45871.25250.066*
C2341.2813 (4)0.5386 (3)1.19082 (17)0.0553 (8)
H2341.32050.60441.22410.066*
C2351.1685 (3)0.5288 (2)1.12438 (16)0.0483 (7)
H2351.13150.58781.11290.058*
C2361.1106 (3)0.4314 (2)1.07503 (14)0.0407 (7)
H2361.03560.42521.03000.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C170.0435 (17)0.0418 (17)0.049 (2)0.0131 (14)0.0166 (15)0.0177 (15)
O170.0615 (13)0.0640 (14)0.0417 (13)0.0025 (11)0.0148 (10)0.0154 (11)
C110.0411 (16)0.0343 (16)0.0530 (19)0.0115 (13)0.0162 (14)0.0161 (14)
C120.0451 (17)0.0414 (17)0.052 (2)0.0145 (14)0.0194 (15)0.0125 (15)
C130.0477 (19)0.047 (2)0.068 (2)0.0107 (16)0.0124 (17)0.0033 (18)
C140.0450 (19)0.0430 (19)0.092 (3)0.0005 (15)0.0214 (19)0.0108 (19)
C150.054 (2)0.054 (2)0.078 (3)0.0049 (17)0.0275 (19)0.0261 (19)
C160.0503 (18)0.0481 (18)0.061 (2)0.0100 (16)0.0211 (16)0.0213 (16)
O120.0589 (13)0.0593 (13)0.0435 (13)0.0011 (11)0.0131 (10)0.0079 (11)
C180.071 (2)0.085 (3)0.047 (2)0.010 (2)0.0170 (18)0.0030 (19)
N110.0439 (14)0.0374 (13)0.0422 (16)0.0061 (11)0.0118 (11)0.0104 (12)
S1110.0529 (5)0.0507 (5)0.0370 (4)0.0070 (4)0.0127 (3)0.0135 (4)
C1120.0342 (15)0.0396 (16)0.0397 (16)0.0116 (13)0.0093 (12)0.0102 (13)
C1130.0368 (15)0.0321 (15)0.0353 (16)0.0077 (12)0.0108 (12)0.0080 (13)
C13A0.0391 (15)0.0356 (15)0.0380 (17)0.0122 (13)0.0130 (13)0.0100 (13)
C1140.0429 (17)0.0464 (17)0.0443 (18)0.0028 (14)0.0135 (14)0.0066 (14)
C1150.0527 (19)0.058 (2)0.052 (2)0.0011 (16)0.0125 (16)0.0047 (16)
C1160.057 (2)0.057 (2)0.056 (2)0.0008 (16)0.0158 (17)0.0027 (17)
C1170.060 (2)0.0520 (19)0.0429 (19)0.0054 (16)0.0075 (15)0.0019 (15)
C17A0.0444 (16)0.0386 (16)0.0397 (17)0.0085 (13)0.0096 (13)0.0059 (13)
C1370.0434 (16)0.0387 (17)0.0368 (17)0.0107 (14)0.0142 (13)0.0069 (14)
O1370.0811 (15)0.0413 (13)0.0447 (13)0.0050 (11)0.0188 (11)0.0035 (10)
C1310.0362 (15)0.0428 (17)0.0309 (16)0.0054 (13)0.0061 (12)0.0062 (13)
C1320.0522 (18)0.0560 (19)0.0365 (17)0.0099 (15)0.0125 (14)0.0096 (15)
C1330.061 (2)0.083 (3)0.042 (2)0.001 (2)0.0105 (16)0.0200 (19)
C1340.058 (2)0.078 (3)0.053 (2)0.0005 (19)0.0025 (17)0.037 (2)
C1350.0419 (18)0.050 (2)0.082 (3)0.0113 (15)0.0009 (17)0.0280 (19)
C1360.0420 (17)0.0532 (19)0.0469 (18)0.0117 (14)0.0095 (14)0.0114 (16)
C270.0414 (17)0.0390 (17)0.0436 (19)0.0108 (14)0.0077 (14)0.0070 (14)
O270.0591 (13)0.0657 (15)0.0460 (14)0.0058 (11)0.0010 (11)0.0110 (11)
C210.0379 (16)0.0377 (16)0.0511 (19)0.0125 (13)0.0135 (14)0.0115 (14)
C220.0424 (17)0.0389 (17)0.059 (2)0.0167 (14)0.0171 (15)0.0156 (15)
C230.062 (2)0.055 (2)0.080 (3)0.0189 (18)0.0327 (19)0.0316 (19)
C240.059 (2)0.050 (2)0.108 (3)0.0067 (18)0.037 (2)0.026 (2)
C250.053 (2)0.047 (2)0.100 (3)0.0028 (16)0.018 (2)0.009 (2)
C260.0520 (19)0.0461 (19)0.066 (2)0.0068 (16)0.0067 (17)0.0024 (17)
O220.0563 (13)0.0579 (13)0.0445 (13)0.0027 (11)0.0089 (10)0.0170 (10)
C280.071 (2)0.086 (3)0.044 (2)0.0231 (19)0.0141 (17)0.0247 (18)
N210.0408 (13)0.0384 (13)0.0355 (13)0.0070 (11)0.0073 (11)0.0087 (11)
S2110.0495 (4)0.0447 (4)0.0367 (4)0.0085 (4)0.0105 (3)0.0063 (3)
C2120.0388 (15)0.0351 (15)0.0373 (16)0.0123 (13)0.0130 (13)0.0088 (13)
C2130.0376 (15)0.0305 (15)0.0351 (16)0.0108 (12)0.0089 (12)0.0051 (12)
C23A0.0398 (15)0.0326 (15)0.0379 (17)0.0109 (13)0.0129 (13)0.0040 (13)
C2140.0449 (17)0.0453 (18)0.0529 (19)0.0067 (14)0.0170 (15)0.0075 (15)
C2150.057 (2)0.064 (2)0.062 (2)0.0002 (17)0.0284 (18)0.0125 (18)
C2160.071 (2)0.062 (2)0.062 (2)0.0062 (19)0.0299 (19)0.0231 (18)
C2170.063 (2)0.0466 (18)0.051 (2)0.0134 (16)0.0260 (16)0.0122 (15)
C27A0.0472 (16)0.0396 (16)0.0423 (18)0.0144 (14)0.0174 (14)0.0065 (14)
C2370.0365 (15)0.0385 (16)0.0418 (17)0.0121 (13)0.0093 (13)0.0099 (14)
O2370.0694 (14)0.0410 (12)0.0494 (13)0.0107 (10)0.0034 (10)0.0160 (10)
C2310.0350 (15)0.0392 (16)0.0338 (16)0.0077 (12)0.0107 (12)0.0096 (13)
C2320.0474 (17)0.0466 (18)0.0383 (17)0.0097 (14)0.0074 (14)0.0141 (15)
C2330.0528 (19)0.066 (2)0.0354 (18)0.0049 (17)0.0058 (14)0.0090 (16)
C2340.060 (2)0.0483 (19)0.049 (2)0.0040 (16)0.0181 (16)0.0013 (16)
C2350.0531 (18)0.0462 (18)0.0510 (19)0.0199 (15)0.0192 (15)0.0085 (16)
C2360.0438 (16)0.0439 (17)0.0355 (16)0.0152 (14)0.0098 (13)0.0087 (14)
Geometric parameters (Å, º) top
C17—O171.224 (3)C27—O271.228 (3)
C17—N111.360 (3)C27—N211.354 (3)
C17—C111.484 (4)C27—C211.493 (4)
C11—C161.395 (4)C21—C221.395 (4)
C11—C121.397 (4)C21—C261.396 (4)
C12—O121.355 (3)C22—O221.354 (3)
C12—C131.386 (4)C22—C231.386 (4)
C13—C141.374 (4)C23—C241.372 (4)
C13—H130.96 (3)C23—H230.9300
C14—C151.364 (4)C24—C251.361 (5)
C14—H140.9300C24—H240.9300
C15—C161.370 (4)C25—C261.379 (4)
C15—H150.9300C25—H250.9300
C16—H160.9300C26—H260.9300
O12—C181.423 (3)O22—C281.423 (3)
C18—H18A0.9600C28—H28A0.9600
C18—H18B0.9600C28—H28B0.9600
C18—H18C0.9600C28—H28C0.9600
N11—C1121.382 (3)N21—C2121.373 (3)
N11—H110.8600N21—H210.8600
S111—C1121.714 (3)S211—C2121.720 (3)
S111—C17A1.725 (3)S211—C27A1.722 (3)
C112—C1131.376 (3)C212—C2131.382 (3)
C113—C13A1.451 (3)C213—C23A1.444 (3)
C113—C1371.459 (3)C213—C2371.472 (3)
C13A—C17A1.357 (3)C23A—C27A1.356 (3)
C13A—C1141.498 (3)C23A—C2141.505 (4)
C114—C1151.512 (4)C214—C2151.516 (4)
C114—H11A0.9700C214—H21A0.9700
C114—H11B0.9700C214—H21B0.9700
C115—C1161.490 (4)C215—C2161.501 (4)
C115—H11C0.9700C215—H21C0.9700
C115—H11D0.9700C215—H21D0.9700
C116—C1171.525 (4)C216—C2171.512 (4)
C116—H11E0.9700C216—H21E0.9700
C116—H11F0.9700C216—H21F0.9700
C117—C17A1.495 (4)C217—C27A1.500 (4)
C117—H11G0.9700C217—H21G0.9700
C117—H11H0.9700C217—H21H0.9700
C137—O1371.227 (3)C237—O2371.227 (3)
C137—C1311.489 (4)C237—C2311.486 (3)
C131—C1321.379 (4)C231—C2361.378 (3)
C131—C1361.380 (4)C231—C2321.390 (3)
C132—C1331.366 (4)C232—C2331.374 (4)
C132—H1320.9300C232—H2320.9300
C133—C1341.363 (4)C233—C2341.373 (4)
C133—H1330.9300C233—H2330.9300
C134—C1351.370 (4)C234—C2351.379 (4)
C134—H1340.9300C234—H2340.9300
C135—C1361.385 (4)C235—C2361.378 (4)
C135—H1350.9300C235—H2350.9300
C136—H1360.9300C236—H2360.9300
O17—C17—N11120.3 (3)O27—C27—N21120.1 (3)
O17—C17—C11121.5 (3)O27—C27—C21121.0 (3)
N11—C17—C11118.1 (3)N21—C27—C21118.9 (3)
C16—C11—C12117.7 (3)C22—C21—C26118.1 (3)
C16—C11—C17115.3 (3)C22—C21—C27125.8 (3)
C12—C11—C17126.9 (3)C26—C21—C27116.0 (3)
O12—C12—C13123.1 (3)O22—C22—C23123.1 (3)
O12—C12—C11117.0 (2)O22—C22—C21117.0 (2)
C13—C12—C11119.9 (3)C23—C22—C21119.9 (3)
C14—C13—C12120.3 (3)C24—C23—C22120.3 (3)
C14—C13—H13119.6 (18)C24—C23—H23119.8
C12—C13—H13120.0 (18)C22—C23—H23119.8
C15—C14—C13120.8 (3)C25—C24—C23120.8 (3)
C15—C14—H14119.6C25—C24—H24119.6
C13—C14—H14119.6C23—C24—H24119.6
C14—C15—C16119.2 (3)C24—C25—C26119.6 (3)
C14—C15—H15120.4C24—C25—H25120.2
C16—C15—H15120.4C26—C25—H25120.2
C15—C16—C11122.1 (3)C25—C26—C21121.2 (3)
C15—C16—H16119.0C25—C26—H26119.4
C11—C16—H16119.0C21—C26—H26119.4
C12—O12—C18120.5 (2)C22—O22—C28119.9 (2)
O12—C18—H18A109.5O22—C28—H28A109.5
O12—C18—H18B109.5O22—C28—H28B109.5
H18A—C18—H18B109.5H28A—C28—H28B109.5
O12—C18—H18C109.5O22—C28—H28C109.5
H18A—C18—H18C109.5H28A—C28—H28C109.5
H18B—C18—H18C109.5H28B—C28—H28C109.5
C17—N11—C112124.3 (2)C27—N21—C212125.1 (2)
C17—N11—H11117.9C27—N21—H21117.5
C112—N11—H11117.9C212—N21—H21117.5
C112—S111—C17A90.94 (13)C212—S211—C27A91.15 (13)
C113—C112—N11125.1 (2)N21—C212—C213125.4 (2)
C113—C112—S111112.8 (2)N21—C212—S211122.28 (19)
N11—C112—S111122.0 (2)C213—C212—S211112.33 (19)
C112—C113—C13A111.4 (2)C212—C213—C23A111.3 (2)
C112—C113—C137121.1 (2)C212—C213—C237120.3 (2)
C13A—C113—C137127.5 (2)C23A—C213—C237128.4 (2)
C17A—C13A—C113111.6 (2)C27A—C23A—C213112.2 (2)
C17A—C13A—C114120.5 (2)C27A—C23A—C214120.3 (2)
C113—C13A—C114127.8 (2)C213—C23A—C214127.4 (2)
C13A—C114—C115112.2 (2)C23A—C214—C215111.5 (2)
C13A—C114—H11A109.2C23A—C214—H21A109.3
C115—C114—H11A109.2C215—C214—H21A109.3
C13A—C114—H11B109.2C23A—C214—H21B109.3
C115—C114—H11B109.2C215—C214—H21B109.3
H11A—C114—H11B107.9H21A—C214—H21B108.0
C116—C115—C114112.6 (3)C216—C215—C214111.2 (2)
C116—C115—H11C109.1C216—C215—H21C109.4
C114—C115—H11C109.1C214—C215—H21C109.4
C116—C115—H11D109.1C216—C215—H21D109.4
C114—C115—H11D109.1C214—C215—H21D109.4
H11C—C115—H11D107.8H21C—C215—H21D108.0
C115—C116—C117112.0 (3)C215—C216—C217112.1 (3)
C115—C116—H11E109.2C215—C216—H21E109.2
C117—C116—H11E109.2C217—C216—H21E109.2
C115—C116—H11F109.2C215—C216—H21F109.2
C117—C116—H11F109.2C217—C216—H21F109.2
H11E—C116—H11F107.9H21E—C216—H21F107.9
C17A—C117—C116109.6 (2)C27A—C217—C216110.3 (2)
C17A—C117—H11G109.7C27A—C217—H21G109.6
C116—C117—H11G109.7C216—C217—H21G109.6
C17A—C117—H11H109.7C27A—C217—H21H109.6
C116—C117—H11H109.7C216—C217—H21H109.6
H11G—C117—H11H108.2H21G—C217—H21H108.1
C13A—C17A—C117126.4 (3)C23A—C27A—C217126.1 (3)
C13A—C17A—S111113.2 (2)C23A—C27A—S211112.9 (2)
C117—C17A—S111120.3 (2)C217—C27A—S211121.0 (2)
O137—C137—C113121.6 (2)O237—C237—C213120.9 (2)
O137—C137—C131117.3 (2)O237—C237—C231118.6 (2)
C113—C137—C131121.0 (2)C213—C237—C231120.4 (2)
C132—C131—C136119.0 (3)C236—C231—C232119.1 (2)
C132—C131—C137119.4 (2)C236—C231—C237121.2 (2)
C136—C131—C137121.4 (2)C232—C231—C237119.5 (2)
C133—C132—C131120.5 (3)C233—C232—C231120.5 (3)
C133—C132—H132119.7C233—C232—H232119.8
C131—C132—H132119.7C231—C232—H232119.8
C134—C133—C132120.6 (3)C234—C233—C232119.9 (3)
C134—C133—H133119.7C234—C233—H233120.1
C132—C133—H133119.7C232—C233—H233120.1
C133—C134—C135120.1 (3)C233—C234—C235120.2 (3)
C133—C134—H134120.0C233—C234—H234119.9
C135—C134—H134120.0C235—C234—H234119.9
C134—C135—C136119.8 (3)C236—C235—C234119.9 (3)
C134—C135—H135120.1C236—C235—H235120.1
C136—C135—H135120.1C234—C235—H235120.1
C131—C136—C135120.1 (3)C231—C236—C235120.5 (3)
C131—C136—H136119.9C231—C236—H236119.8
C135—C136—H136119.9C235—C236—H236119.8
O17—C17—C11—C163.8 (4)O27—C27—C21—C22173.8 (3)
N11—C17—C11—C16177.2 (2)N21—C27—C21—C225.0 (4)
O17—C17—C11—C12173.4 (3)O27—C27—C21—C263.6 (4)
N11—C17—C11—C125.6 (4)N21—C27—C21—C26177.7 (2)
C16—C11—C12—O12179.3 (2)C26—C21—C22—O22179.3 (2)
C17—C11—C12—O123.6 (4)C27—C21—C22—O223.4 (4)
C16—C11—C12—C131.6 (4)C26—C21—C22—C230.8 (4)
C17—C11—C12—C13175.5 (3)C27—C21—C22—C23176.5 (2)
O12—C12—C13—C14179.0 (3)O22—C22—C23—C24179.3 (3)
C11—C12—C13—C141.9 (4)C21—C22—C23—C240.8 (4)
C12—C13—C14—C150.8 (5)C22—C23—C24—C250.5 (5)
C13—C14—C15—C160.6 (5)C23—C24—C25—C260.3 (5)
C14—C15—C16—C110.9 (4)C24—C25—C26—C210.3 (5)
C12—C11—C16—C150.2 (4)C22—C21—C26—C250.5 (4)
C17—C11—C16—C15177.3 (2)C27—C21—C26—C25177.0 (3)
C13—C12—O12—C182.0 (4)C23—C22—O22—C280.7 (4)
C11—C12—O12—C18177.1 (2)C21—C22—O22—C28179.3 (2)
O17—C17—N11—C1122.4 (4)O27—C27—N21—C2120.6 (4)
C11—C17—N11—C112176.7 (2)C21—C27—N21—C212178.2 (2)
C17—N11—C112—C113175.4 (2)C27—N21—C212—C213176.4 (2)
C17—N11—C112—S1111.9 (3)C27—N21—C212—S2112.5 (3)
C17A—S111—C112—C1132.9 (2)C27A—S211—C212—N21177.5 (2)
C17A—S111—C112—N11179.6 (2)C27A—S211—C212—C2133.48 (19)
N11—C112—C113—C13A179.3 (2)N21—C212—C213—C23A177.6 (2)
S111—C112—C113—C13A3.2 (3)S211—C212—C213—C23A3.4 (3)
N11—C112—C113—C1371.6 (4)N21—C212—C213—C2373.5 (4)
S111—C112—C113—C137175.89 (18)S211—C212—C213—C237175.46 (17)
C112—C113—C13A—C17A1.9 (3)C212—C213—C23A—C27A1.4 (3)
C137—C113—C13A—C17A177.2 (2)C237—C213—C23A—C27A177.3 (2)
C112—C113—C13A—C114173.7 (2)C212—C213—C23A—C214174.1 (2)
C137—C113—C13A—C1147.3 (4)C237—C213—C23A—C2147.1 (4)
C17A—C13A—C114—C11513.8 (4)C27A—C23A—C214—C21516.8 (4)
C113—C13A—C114—C115161.4 (2)C213—C23A—C214—C215158.4 (2)
C13A—C114—C115—C11644.5 (3)C23A—C214—C215—C21648.3 (3)
C114—C115—C116—C11761.3 (4)C214—C215—C216—C21763.0 (3)
C115—C116—C117—C17A43.5 (3)C215—C216—C217—C27A41.9 (3)
C113—C13A—C17A—C117177.0 (2)C213—C23A—C27A—C217178.1 (2)
C114—C13A—C17A—C1171.1 (4)C214—C23A—C27A—C2172.1 (4)
C113—C13A—C17A—S1110.3 (3)C213—C23A—C27A—S2111.2 (3)
C114—C13A—C17A—S111176.23 (19)C214—C23A—C27A—S211177.12 (19)
C116—C117—C17A—C13A13.7 (4)C216—C217—C27A—C23A10.3 (4)
C116—C117—C17A—S111169.2 (2)C216—C217—C27A—S211170.5 (2)
C112—S111—C17A—C13A1.8 (2)C212—S211—C27A—C23A2.7 (2)
C112—S111—C17A—C117175.7 (2)C212—S211—C27A—C217176.7 (2)
C112—C113—C137—O13723.8 (4)C212—C213—C237—O23729.9 (4)
C13A—C113—C137—O137157.3 (3)C23A—C213—C237—O237151.4 (2)
C112—C113—C137—C131152.9 (2)C212—C213—C237—C231145.6 (2)
C13A—C113—C137—C13126.1 (4)C23A—C213—C237—C23133.0 (4)
O137—C137—C131—C13242.1 (4)O237—C237—C231—C236141.3 (3)
C113—C137—C131—C132141.1 (3)C213—C237—C231—C23634.3 (4)
O137—C137—C131—C136132.0 (3)O237—C237—C231—C23233.6 (4)
C113—C137—C131—C13644.8 (4)C213—C237—C231—C232150.8 (2)
C136—C131—C132—C1330.2 (4)C236—C231—C232—C2330.1 (4)
C137—C131—C132—C133174.4 (3)C237—C231—C232—C233175.1 (2)
C131—C132—C133—C1341.0 (5)C231—C232—C233—C2340.9 (4)
C132—C133—C134—C1350.4 (5)C232—C233—C234—C2350.8 (4)
C133—C134—C135—C1360.9 (5)C233—C234—C235—C2360.1 (4)
C132—C131—C136—C1351.2 (4)C232—C231—C236—C2350.7 (4)
C137—C131—C136—C135173.0 (2)C237—C231—C236—C235174.1 (2)
C134—C135—C136—C1311.7 (4)C234—C235—C236—C2310.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O120.861.952.630 (3)136
N11—H11···O1370.862.112.731 (3)128
N21—H21···O220.861.932.616 (3)136
N21—H21···O2370.862.132.748 (3)129
C134—H134···O270.932.493.232 (4)137
C235—H235···Cg3i0.932.953.869 (3)170
Symmetry code: (i) x+2, y+1, z+2.
2-Amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene (VI) top
Crystal data top
C15H15NOSDx = 1.273 Mg m3
Mr = 257.34Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pna21Cell parameters from 3556 reflections
a = 9.2080 (4) Åθ = 3.3–28.2°
b = 14.0485 (7) ŵ = 0.23 mm1
c = 10.3826 (6) ÅT = 295 K
V = 1343.08 (12) Å3Block, colourless
Z = 40.30 × 0.15 × 0.15 mm
F(000) = 544
Data collection top
Agilent Eos Gemini
diffractometer
1720 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.021
φ and ω scansθmax = 28.2°, θmin = 3.3°
Absorption correction: multi-scan
CrysAlis RED (Agilent, 2012)
h = 1111
Tmin = 0.948, Tmax = 0.966k = 717
3556 measured reflectionsl = 813
1984 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.1113P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.13 e Å3
1984 reflectionsΔρmin = 0.23 e Å3
176 parametersAbsolute structure: Flack x determined using 422 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
13 restraintsAbsolute structure parameter: 0.03 (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*/UeqOcc. (<1)
S10.01074 (7)0.60683 (5)0.43072 (12)0.0549 (2)
C20.1557 (3)0.6376 (2)0.3673 (3)0.0439 (7)
C30.2490 (3)0.55885 (19)0.3594 (3)0.0377 (6)
C3A0.1817 (3)0.47431 (19)0.4150 (3)0.0397 (6)0.887 (9)
C40.2556 (5)0.3800 (4)0.4395 (11)0.0546 (9)0.887 (9)
H4A0.35490.39100.46710.066*0.887 (9)
H4B0.25830.34340.36040.066*0.887 (9)
C50.1742 (4)0.3240 (3)0.5432 (6)0.0645 (15)0.887 (9)
H5A0.21200.25960.54700.077*0.887 (9)
H5B0.19000.35360.62650.077*0.887 (9)
C60.0132 (4)0.3210 (3)0.5147 (6)0.0682 (16)0.887 (9)
H6A0.03480.27880.57510.082*0.887 (9)
H6B0.00250.29660.42840.082*0.887 (9)
C70.0508 (5)0.4208 (4)0.5257 (10)0.0624 (10)0.887 (9)
H7A0.14760.42180.48900.075*0.887 (9)
H7B0.05760.43900.61560.075*0.887 (9)
C7A0.0453 (3)0.4895 (2)0.4549 (3)0.0458 (7)0.887 (9)
C23A0.1817 (3)0.47431 (19)0.4150 (3)0.0397 (6)0.113 (9)
C240.260 (3)0.383 (2)0.445 (7)0.0546 (9)0.113 (9)
H24A0.32590.39270.51700.066*0.113 (9)
H24B0.31690.36300.37140.066*0.113 (9)
C250.151 (3)0.3044 (10)0.480 (3)0.0645 (15)0.113 (9)
H25A0.09940.28470.40290.077*0.113 (9)
H25B0.20240.24960.51380.077*0.113 (9)
C260.044 (3)0.3399 (15)0.579 (3)0.0682 (16)0.113 (9)
H26A0.09540.36450.65310.082*0.113 (9)
H26B0.01730.28760.60740.082*0.113 (9)
C270.051 (3)0.418 (2)0.521 (7)0.0624 (10)0.113 (9)
H27A0.11840.39090.45970.075*0.113 (9)
H27B0.10630.44920.58850.075*0.113 (9)
C27A0.0453 (3)0.4895 (2)0.4549 (3)0.0458 (7)0.113 (9)
N20.1839 (3)0.72731 (17)0.3320 (3)0.0586 (7)
H2A0.26740.74180.30050.070*
H2B0.11850.77050.34100.070*
C370.3896 (3)0.5705 (2)0.3022 (3)0.0444 (7)
O370.4441 (2)0.65081 (16)0.2880 (3)0.0665 (7)
C310.4730 (3)0.4869 (2)0.2516 (3)0.0448 (7)
C320.6207 (3)0.4802 (3)0.2752 (4)0.0637 (10)
H320.66680.52580.32560.076*
C330.6992 (4)0.4058 (3)0.2237 (5)0.0843 (13)
H330.79810.40070.24040.101*
C340.6313 (5)0.3388 (3)0.1474 (5)0.0834 (13)
H340.68420.28820.11370.100*
C350.4867 (4)0.3466 (3)0.1214 (4)0.0726 (11)
H350.44160.30250.06790.087*
C360.4079 (4)0.4196 (2)0.1740 (4)0.0573 (8)
H360.30890.42390.15710.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0484 (3)0.0496 (4)0.0667 (5)0.0123 (3)0.0063 (4)0.0006 (5)
C20.0470 (15)0.0387 (15)0.0459 (16)0.0003 (13)0.0054 (14)0.0016 (14)
C30.0396 (13)0.0323 (13)0.0411 (15)0.0012 (12)0.0030 (11)0.0008 (13)
C3A0.0426 (11)0.0355 (13)0.0409 (16)0.0002 (11)0.0000 (13)0.0013 (14)
C40.0520 (14)0.0404 (16)0.071 (2)0.0046 (12)0.0094 (19)0.0110 (19)
C50.067 (2)0.051 (2)0.076 (4)0.0078 (19)0.013 (2)0.024 (2)
C60.066 (2)0.054 (2)0.084 (4)0.0099 (19)0.019 (2)0.021 (3)
C70.0488 (16)0.067 (2)0.071 (2)0.0030 (16)0.0158 (16)0.016 (2)
C7A0.0434 (12)0.0446 (16)0.0494 (19)0.0010 (11)0.0033 (14)0.0052 (15)
C23A0.0426 (11)0.0355 (13)0.0409 (16)0.0002 (11)0.0000 (13)0.0013 (14)
C240.0520 (14)0.0404 (16)0.071 (2)0.0046 (12)0.0094 (19)0.0110 (19)
C250.067 (2)0.051 (2)0.076 (4)0.0078 (19)0.013 (2)0.024 (2)
C260.066 (2)0.054 (2)0.084 (4)0.0099 (19)0.019 (2)0.021 (3)
C270.0488 (16)0.067 (2)0.071 (2)0.0030 (16)0.0158 (16)0.016 (2)
C27A0.0434 (12)0.0446 (16)0.0494 (19)0.0010 (11)0.0033 (14)0.0052 (15)
N20.0606 (14)0.0332 (14)0.082 (2)0.0061 (12)0.0000 (14)0.0055 (15)
C370.0420 (13)0.0399 (16)0.0514 (17)0.0059 (13)0.0039 (13)0.0056 (15)
O370.0547 (12)0.0414 (13)0.104 (2)0.0117 (11)0.0080 (13)0.0090 (14)
C310.0467 (14)0.0439 (17)0.0439 (17)0.0007 (13)0.0076 (13)0.0072 (15)
C320.0475 (15)0.074 (2)0.070 (3)0.0010 (16)0.0045 (16)0.000 (2)
C330.058 (2)0.099 (3)0.096 (3)0.025 (2)0.021 (2)0.013 (3)
C340.101 (3)0.071 (3)0.078 (3)0.021 (2)0.038 (3)0.002 (2)
C350.091 (3)0.065 (3)0.062 (2)0.000 (2)0.018 (2)0.014 (2)
C360.0590 (17)0.059 (2)0.0542 (19)0.0043 (16)0.0060 (17)0.0061 (18)
Geometric parameters (Å, º) top
S1—C21.723 (3)C25—C261.511 (8)
S1—C7A1.745 (3)C25—H25A0.9700
C2—N21.338 (4)C25—H25B0.9700
C2—C31.403 (4)C26—C271.524 (9)
C3—C371.433 (4)C26—H26A0.9700
C3—C3A1.459 (4)C26—H26B0.9700
C3A—C7A1.339 (3)C27—H27A0.9700
C3A—C41.511 (4)C27—H27B0.9700
C4—C51.531 (7)N2—H2A0.8600
C4—H4A0.9700N2—H2B0.8600
C4—H4B0.9700C37—O371.244 (3)
C5—C61.513 (6)C37—C311.498 (4)
C5—H5A0.9700C31—C361.379 (4)
C5—H5B0.9700C31—C321.386 (4)
C6—C71.524 (7)C32—C331.379 (5)
C6—H6A0.9700C32—H320.9300
C6—H6B0.9700C33—C341.379 (6)
C7—C7A1.502 (4)C33—H330.9300
C7—H7A0.9700C34—C351.363 (5)
C7—H7B0.9700C34—H340.9300
C24—C251.531 (9)C35—C361.370 (5)
C24—H24A0.9700C35—H350.9300
C24—H24B0.9700C36—H360.9300
C2—S1—C7A91.63 (13)C26—C25—C24110.6 (11)
N2—C2—C3127.5 (3)C26—C25—H25A109.5
N2—C2—S1120.9 (2)C24—C25—H25A109.5
C3—C2—S1111.7 (2)C26—C25—H25B109.5
C2—C3—C37119.2 (3)C24—C25—H25B109.5
C2—C3—C3A111.0 (2)H25A—C25—H25B108.1
C37—C3—C3A129.8 (2)C25—C26—C27110.1 (11)
C7A—C3A—C3113.0 (2)C25—C26—H26A109.7
C7A—C3A—C4120.7 (3)C27—C26—H26A109.7
C3—C3A—C4126.1 (2)C25—C26—H26B109.7
C3A—C4—C5110.4 (4)C27—C26—H26B109.7
C3A—C4—H4A109.6H26A—C26—H26B108.2
C5—C4—H4A109.6C26—C27—H27A109.9
C3A—C4—H4B109.6C26—C27—H27B109.9
C5—C4—H4B109.6H27A—C27—H27B108.3
H4A—C4—H4B108.1C2—N2—H2A120.0
C6—C5—C4110.9 (6)C2—N2—H2B120.0
C6—C5—H5A109.5H2A—N2—H2B120.0
C4—C5—H5A109.5O37—C37—C3121.1 (3)
C6—C5—H5B109.5O37—C37—C31117.5 (3)
C4—C5—H5B109.5C3—C37—C31121.3 (3)
H5A—C5—H5B108.1C36—C31—C32118.9 (3)
C5—C6—C7109.8 (6)C36—C31—C37121.3 (3)
C5—C6—H6A109.7C32—C31—C37119.6 (3)
C7—C6—H6A109.7C33—C32—C31119.8 (4)
C5—C6—H6B109.7C33—C32—H32120.1
C7—C6—H6B109.7C31—C32—H32120.1
H6A—C6—H6B108.2C34—C33—C32120.1 (4)
C7A—C7—C6109.1 (4)C34—C33—H33119.9
C7A—C7—H7A109.9C32—C33—H33119.9
C6—C7—H7A109.9C35—C34—C33120.1 (4)
C7A—C7—H7B109.9C35—C34—H34119.9
C6—C7—H7B109.9C33—C34—H34119.9
H7A—C7—H7B108.3C34—C35—C36119.9 (4)
C3A—C7A—C7126.9 (3)C34—C35—H35120.0
C3A—C7A—S1112.6 (2)C36—C35—H35120.0
C7—C7A—S1120.2 (2)C35—C36—C31121.1 (3)
C25—C24—H24A109.6C35—C36—H36119.5
C25—C24—H24B109.6C31—C36—H36119.5
H24A—C24—H24B108.1
C7A—S1—C2—N2177.3 (3)C6—C7—C7A—S1171.3 (5)
C7A—S1—C2—C32.7 (2)C2—S1—C7A—C3A1.0 (3)
N2—C2—C3—C373.4 (5)C2—S1—C7A—C7173.3 (6)
S1—C2—C3—C37176.6 (2)C24—C25—C26—C2766.1 (18)
N2—C2—C3—C3A176.4 (3)C2—C3—C37—O3717.5 (4)
S1—C2—C3—C3A3.7 (3)C3A—C3—C37—O37162.2 (3)
C2—C3—C3A—C7A3.0 (4)C2—C3—C37—C31159.5 (3)
C37—C3—C3A—C7A177.3 (3)C3A—C3—C37—C3120.8 (5)
C2—C3—C3A—C4171.5 (6)O37—C37—C31—C36130.1 (3)
C37—C3—C3A—C48.2 (8)C3—C37—C31—C3647.0 (5)
C7A—C3A—C4—C516.5 (11)O37—C37—C31—C3245.3 (4)
C3—C3A—C4—C5157.6 (5)C3—C37—C31—C32137.6 (3)
C3A—C4—C5—C649.0 (11)C36—C31—C32—C331.5 (5)
C4—C5—C6—C766.4 (11)C37—C31—C32—C33177.0 (3)
C5—C6—C7—C7A46.7 (11)C31—C32—C33—C340.9 (6)
C3—C3A—C7A—C7174.7 (6)C32—C33—C34—C350.8 (6)
C4—C3A—C7A—C70.1 (10)C33—C34—C35—C361.8 (7)
C3—C3A—C7A—S10.9 (3)C34—C35—C36—C311.2 (6)
C4—C3A—C7A—S1173.9 (6)C32—C31—C36—C350.5 (6)
C6—C7—C7A—C3A15.3 (11)C37—C31—C36—C35175.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O370.862.072.666 (3)125
N2—H2B···O37i0.862.032.831 (3)156
Symmetry code: (i) x1/2, y+3/2, z.
Selected geometric parameters (Å, °) for compounds (I)–(VI) top
(a)Ring-puckering parameters
Qθφ
(I), major0.516 (5)49.0 (6)145.5 (8)
(I), minor0.50 (2)139 (2)332 (4)
(II), major0.514 (9)48.3 (11)150.4 (17)
(II), minor0.538 (18)134 (2)330 (3)
(III), major0.507 (5)50.0 (6)138.7 (8)
(III), minor0.489 (19)143 (2)327 (4)
(IV), molecule 10.467 (3)50.7 (4)150.5 (5)
(IV), molecule 20.486 (4)51.5 (4)143.5 (5)
(V)0.5098 (19)53.3 (2)142.2 (2)
(VI), major0.517 (6)49.7 (7)148.9 (9)
(VI), minor0.51 (3)135 (3)331 (6)
(b)Torsion angles
τ1τ2τ3τ4
(I)0.0 (3)179.60 (18)-158.70 (19)-132.4 (2)
(II)6.6 (4)-175.9 (3)-170.5 (3)-110.7 (4)
(III)-7.3 (3)178.76 (18)-134.5 (2)-147.78 (19)
(IV), molecule 1-1.9 (3)-176.7 (2)5.6 (4)-141.1 (3)
(IV), molecule 2-2.5 (3)-178.2 (2)5.0 (4)-150.8 (2)
(V)-2.1 (2)-179.62 (14)-172.35 (14)-148.30 (15)
(VI)-137.6 (3)
For the major- and minor-disorder components in compounds (I)–(III) and (VI), the ring-puckering parameters are calculated for the atom sequences C13A–C14–C15–C16–C17–C17A and C13A–C24–C25–C26–C27–C17A, respectively. For molecules 1 and 2 in compound (IV), the parameters are calculated for the atom sequences C13A–C114–C115–C116–C117–C17A and C23A–C24–C25–C26–C27–C27A, respectively. The parameters for compound (V) have been calculated using the published atomic coordinates (Kaur, Jasinski, Yathirajan et al., 2014), but with the atom labels and the enantiomorph adjusted to match those of the major-disorder components in compounds (I)–(III) and (VI). For compounds (I)–(V), τ1, τ2, τ3 and τ4 represent, respectively, the torsion angles Sx11—Cx12—Nx1—Cx7, Cx12—Nx1—Cx7—Cx1, Nx1—Cx7—Cx1—Cx2 and Cx13—Cx37—Cx31—Cx32, where x is nul for (I)–(III) and (V), and x = 1 or 2 for molecules 1 and 2 in compound (IV). For compound (VI), τ4 represents the torsion angle C3—C37—C31—C32.
Hydrogen bonds and short intramolecular contacts (Å, °) for compounds (I)–(IV) and (VI) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)N1—H1···O370.862.012.650 (3)130
(II)N1—H1···O370.861.992.641 (3)132
C3—H3···Cg1i0.932.763.676 (4)169
C14—H14A···Cg10.972.963.475 (9)114
C24—H24A···Cg10.972.733.530 (17)140
(III)N1—H1···O370.862.082.718 (2)130
C3—H3···O37ii0.932.503.326 (3)148
C17—H17A···O7iii0.972.593.494 (12)156
C4—H4···Cg1iv0.932.853.635 (2)143
C35—H35···Cg2v0.932.753.520 (2)141
(IV)N11—H11···O120.861.952.630 (3)136
N11—H11···O1370.862.112.731 (3)128
N21—H21···O220.861.932.616 (3)136
N21—H21···O2370.862.132.748 (3)129
C134—H134···O270.932.493.232 (4)137
C235—H235···Cg3vi0.932.953.869 (3)170
(VI)N2—H2A···O370.862.072.666 (3)125
N2—H2B···O37vii0.862.032.831 (3)156
Cg1, Cg2 and Cg3 represent the centroids of the rings C31–C36, S11/C12/C13/C13A/C17A and S211/C212/C213/C23A/C27A, respectively.

Symmetry codes: (i) -x+1/2, y-1/2, -z+1/2; (ii) -x+1, -y, -z+1; (iii) -x+1, -y, -z; (iv) -x, -y, -z+1; (v) x-1, y, z; (vi) -x, -y+1, -z+2; (vii) x-1/2, -y+3/2, z.
 

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