Four closely related N-(3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phen-2-yl)benzamides: order versus disorder, and similar mol­ecular conformations but different modes of supra­molecular aggregation, with a new disordered refinement of 2-amino-3-benzoyl-4,5,6,7-tetra­hydro­benzo[b]thio­phene

Sagar, B.K.; Yathirajan, H.S.; Rathore, R.S.; Glidewell, C.

doi:10.1107/S2053229617017326

Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamides: order versus disorder, and similar molecular conformations but different modes of supramolecular aggregation, with a new disordered refinement of 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene

B. K. Sagar, H. S. Yathirajan, R. S. Rathore and C. Glidewell

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.

Keywords: synthesis; benzo[b]thiophenes; crystal structure; molecular conformation; conformational disorder; hydrogen bonding; supramolecular assembly; π–π stacking.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017326/ov3102sup1.cif Contains datablocks global, I, II, III, IV, VI
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017326/ov3102VIsup6.hkl Contains datablock VI
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017326/ov3102Isup7.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017326/ov3102IIsup8.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017326/ov3102IIIsup9.cml Supplementary material
	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

C₂₂H₁₈FNO₂S	F(000) = 792
M_r = 379.43	D_x = 1.371 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.9489 (11) Å	Cell parameters from 5442 reflections
b = 7.2739 (4) Å	θ = 1.3–30.3°
c = 15.9222 (10) Å	µ = 0.20 mm⁻¹
β = 95.813 (4)°	T = 296 K
V = 1837.6 (2) Å³	Block, colourless
Z = 4	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker Kappa APEXII diffractometer	2343 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	R_int = 0.052
φ and ω scans	θ_max = 26.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −20→20
T_min = 0.895, T_max = 0.980	k = −9→9
21151 measured reflections	l = −20→20
3809 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)] = 0.046	w = 1/[σ²(F_o²) + (0.0475P)² + 0.4981P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.122	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.16 e Å⁻³
3809 reflections	Δρ_min = −0.20 e Å⁻³
258 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
12 restraints	Extinction 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C7	0.47949 (13)	0.6101 (3)	0.23133 (15)	0.0465 (6)
O7	0.44771 (10)	0.6398 (3)	0.15993 (11)	0.0692 (5)
C1	0.42894 (13)	0.6016 (3)	0.30528 (14)	0.0429 (5)
C2	0.34324 (14)	0.5665 (3)	0.28845 (16)	0.0532 (6)
H2	0.3192	0.5467	0.2335	0.064*
C3	0.29523 (14)	0.5618 (3)	0.35488 (19)	0.0583 (7)
F3	0.21131 (9)	0.5261 (3)	0.33825 (12)	0.0938 (6)
C4	0.32656 (16)	0.5938 (3)	0.43705 (18)	0.0589 (7)
H4	0.2920	0.5897	0.4806	0.071*
C5	0.41083 (15)	0.6321 (3)	0.45229 (17)	0.0587 (7)
H5	0.4341	0.6563	0.5071	0.070*
C6	0.46162 (14)	0.6352 (3)	0.38704 (15)	0.0514 (6)
H6	0.5188	0.6603	0.3986	0.062*
N1	0.56415 (10)	0.5827 (2)	0.24788 (11)	0.0451 (5)
H1	0.5837	0.5629	0.2994	0.054*
S11	0.59028 (4)	0.62223 (8)	0.08302 (4)	0.0539 (2)
C12	0.62066 (14)	0.5844 (3)	0.18772 (13)	0.0409 (5)
C13	0.70640 (13)	0.5546 (3)	0.20427 (13)	0.0395 (5)
C13A	0.74750 (14)	0.5566 (3)	0.12712 (14)	0.0434 (5)	0.811 (6)
C14	0.8387 (2)	0.5147 (13)	0.1187 (2)	0.0586 (11)	0.811 (6)
H14A	0.8575	0.4166	0.1574	0.070*	0.811 (6)
H14B	0.8726	0.6227	0.1339	0.070*	0.811 (6)
C15	0.8513 (2)	0.4569 (6)	0.0284 (2)	0.0694 (12)	0.811 (6)
H15A	0.9110	0.4503	0.0218	0.083*	0.811 (6)
H15B	0.8269	0.3362	0.0168	0.083*	0.811 (6)
C16	0.8092 (3)	0.5961 (6)	−0.0331 (2)	0.0761 (13)	0.811 (6)
H16A	0.8227	0.5677	−0.0897	0.091*	0.811 (6)
H16B	0.8307	0.7179	−0.0186	0.091*	0.811 (6)
C17	0.7135 (3)	0.5940 (16)	−0.0311 (2)	0.0714 (10)	0.811 (6)
H17A	0.6889	0.7017	−0.0599	0.086*	0.811 (6)
H17B	0.6899	0.4857	−0.0601	0.086*	0.811 (6)
C17A	0.69285 (15)	0.5931 (3)	0.05883 (14)	0.0506 (6)	0.811 (6)
C23A	0.74750 (14)	0.5566 (3)	0.12712 (14)	0.0434 (5)	0.189 (6)
C24	0.8348 (9)	0.495 (6)	0.1092 (7)	0.0586 (11)	0.189 (6)
H24A	0.8384	0.3624	0.1134	0.070*	0.189 (6)
H24B	0.8762	0.5469	0.1516	0.070*	0.189 (6)
C25	0.8558 (7)	0.555 (3)	0.0216 (8)	0.0694 (12)	0.189 (6)
H25A	0.8645	0.6867	0.0213	0.083*	0.189 (6)
H25B	0.9078	0.4961	0.0093	0.083*	0.189 (6)
C26	0.7861 (8)	0.505 (2)	−0.0465 (7)	0.0761 (13)	0.189 (6)
H26A	0.7748	0.3736	−0.0447	0.091*	0.189 (6)
H26B	0.8034	0.5337	−0.1017	0.091*	0.189 (6)
C27	0.7063 (13)	0.613 (7)	−0.0321 (6)	0.0714 (10)	0.189 (6)
H27A	0.7132	0.7411	−0.0461	0.086*	0.189 (6)
H27B	0.6583	0.5642	−0.0675	0.086*	0.189 (6)
C27A	0.69285 (15)	0.5931 (3)	0.05883 (14)	0.0506 (6)	0.189 (6)
C37	0.74366 (14)	0.5196 (3)	0.29015 (14)	0.0456 (5)
O37	0.69952 (10)	0.4827 (3)	0.34774 (10)	0.0662 (5)
C31	0.83655 (14)	0.5287 (3)	0.31342 (14)	0.0490 (6)
C32	0.87614 (17)	0.3885 (4)	0.36015 (17)	0.0771 (9)
H32	0.8457	0.2854	0.3735	0.093*
C33	0.9610 (2)	0.4007 (6)	0.3872 (2)	0.1091 (13)
H33	0.9878	0.3052	0.4182	0.131*
C34	1.0054 (2)	0.5528 (7)	0.3686 (2)	0.1112 (14)
H34	1.0625	0.5604	0.3869	0.133*
C35	0.96709 (19)	0.6936 (6)	0.3235 (2)	0.0901 (11)
H35	0.9978	0.7974	0.3116	0.108*
C36	0.88298 (16)	0.6819 (4)	0.29559 (16)	0.0633 (7)
H36	0.8569	0.7779	0.2644	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0376 (13)	0.0436 (13)	0.0566 (15)	0.0011 (10)	−0.0027 (11)	0.0005 (11)
O7	0.0486 (10)	0.0989 (14)	0.0582 (11)	0.0068 (10)	−0.0046 (8)	0.0119 (10)
C1	0.0333 (12)	0.0363 (12)	0.0578 (14)	0.0029 (9)	−0.0017 (10)	−0.0025 (10)
C2	0.0380 (13)	0.0541 (14)	0.0658 (16)	0.0034 (11)	−0.0026 (12)	−0.0075 (12)
C3	0.0309 (13)	0.0537 (15)	0.091 (2)	0.0032 (11)	0.0084 (13)	−0.0069 (14)
F3	0.0362 (8)	0.1247 (14)	0.1210 (14)	−0.0057 (9)	0.0103 (9)	−0.0185 (11)
C4	0.0507 (15)	0.0548 (15)	0.0740 (18)	0.0080 (12)	0.0201 (14)	−0.0036 (13)
C5	0.0536 (16)	0.0597 (16)	0.0629 (16)	0.0043 (13)	0.0067 (13)	−0.0094 (12)
C6	0.0373 (13)	0.0534 (14)	0.0625 (16)	−0.0019 (11)	0.0002 (11)	−0.0063 (12)
N1	0.0354 (10)	0.0538 (11)	0.0451 (11)	−0.0001 (8)	−0.0001 (8)	−0.0001 (9)
S11	0.0551 (4)	0.0550 (4)	0.0494 (4)	−0.0035 (3)	−0.0051 (3)	0.0073 (3)
C12	0.0440 (13)	0.0354 (11)	0.0428 (12)	−0.0034 (9)	0.0029 (10)	−0.0009 (9)
C13	0.0385 (12)	0.0385 (12)	0.0415 (12)	−0.0032 (9)	0.0043 (10)	−0.0021 (9)
C13A	0.0491 (14)	0.0389 (12)	0.0430 (13)	−0.0039 (10)	0.0083 (11)	−0.0010 (10)
C14	0.0567 (17)	0.069 (2)	0.0538 (17)	0.0025 (14)	0.0213 (14)	−0.0051 (17)
C15	0.072 (2)	0.081 (3)	0.0596 (19)	−0.006 (2)	0.0288 (16)	−0.013 (2)
C16	0.105 (3)	0.073 (3)	0.056 (2)	−0.006 (2)	0.033 (2)	0.008 (2)
C17	0.091 (2)	0.079 (3)	0.0439 (15)	−0.0127 (19)	0.0082 (14)	0.0074 (14)
C17A	0.0610 (15)	0.0470 (13)	0.0438 (13)	−0.0063 (11)	0.0054 (11)	0.0013 (11)
C23A	0.0491 (14)	0.0389 (12)	0.0430 (13)	−0.0039 (10)	0.0083 (11)	−0.0010 (10)
C24	0.0567 (17)	0.069 (2)	0.0538 (17)	0.0025 (14)	0.0213 (14)	−0.0051 (17)
C25	0.072 (2)	0.081 (3)	0.0596 (19)	−0.006 (2)	0.0288 (16)	−0.013 (2)
C26	0.105 (3)	0.073 (3)	0.056 (2)	−0.006 (2)	0.033 (2)	0.008 (2)
C27	0.091 (2)	0.079 (3)	0.0439 (15)	−0.0127 (19)	0.0082 (14)	0.0074 (14)
C27A	0.0610 (15)	0.0470 (13)	0.0438 (13)	−0.0063 (11)	0.0054 (11)	0.0013 (11)
C37	0.0417 (13)	0.0507 (13)	0.0449 (13)	−0.0004 (11)	0.0069 (11)	−0.0020 (11)
O37	0.0436 (10)	0.1099 (15)	0.0458 (10)	−0.0053 (9)	0.0081 (8)	0.0106 (9)
C31	0.0402 (13)	0.0706 (16)	0.0364 (12)	0.0043 (12)	0.0056 (10)	0.0010 (11)
C32	0.0546 (17)	0.109 (2)	0.0678 (18)	0.0135 (17)	0.0090 (14)	0.0293 (17)
C33	0.060 (2)	0.183 (4)	0.084 (2)	0.036 (2)	0.0046 (18)	0.044 (3)
C34	0.0412 (18)	0.220 (5)	0.072 (2)	0.003 (2)	0.0046 (16)	0.001 (3)
C35	0.0554 (19)	0.147 (3)	0.068 (2)	−0.031 (2)	0.0091 (16)	−0.020 (2)
C36	0.0523 (16)	0.0833 (19)	0.0546 (15)	−0.0114 (14)	0.0066 (12)	−0.0084 (14)

Geometric parameters (Å, º) top

C7—O7	1.216 (3)	C16—H16A	0.9700
C7—N1	1.364 (3)	C16—H16B	0.9700
C7—C1	1.494 (3)	C17—C17A	1.502 (3)
C1—C6	1.374 (3)	C17—H17A	0.9700
C1—C2	1.390 (3)	C17—H17B	0.9700
C2—C3	1.368 (3)	C24—C25	1.529 (7)
C2—H2	0.9300	C24—H24A	0.9700
C3—F3	1.363 (3)	C24—H24B	0.9700
C3—C4	1.372 (4)	C25—C26	1.517 (6)
C4—C5	1.370 (3)	C25—H25A	0.9700
C4—H4	0.9300	C25—H25B	0.9700
C5—C6	1.381 (3)	C26—C27	1.532 (8)
C5—H5	0.9300	C26—H26A	0.9700
C6—H6	0.9300	C26—H26B	0.9700
N1—C12	1.380 (3)	C27—H27A	0.9700
N1—H1	0.8600	C27—H27B	0.9700
S11—C12	1.711 (2)	C37—O37	1.241 (2)
S11—C17A	1.731 (2)	C37—C31	1.492 (3)
C12—C13	1.383 (3)	C31—C32	1.377 (3)
C13—C13A	1.450 (3)	C31—C36	1.383 (3)
C13—C37	1.457 (3)	C32—C33	1.380 (4)
C13A—C17A	1.349 (3)	C32—H32	0.9300
C13A—C14	1.505 (3)	C33—C34	1.363 (5)
C14—C15	1.531 (5)	C33—H33	0.9300
C14—H14A	0.9700	C34—C35	1.360 (5)
C14—H14B	0.9700	C34—H34	0.9300
C15—C16	1.517 (5)	C35—C36	1.372 (4)
C15—H15A	0.9700	C35—H35	0.9300
C15—H15B	0.9700	C36—H36	0.9300
C16—C17	1.530 (7)

O7—C7—N1	121.2 (2)	C17—C16—H16B	109.5
O7—C7—C1	122.5 (2)	H16A—C16—H16B	108.0
N1—C7—C1	116.4 (2)	C17A—C17—C16	109.6 (4)
C6—C1—C2	119.1 (2)	C17A—C17—H17A	109.8
C6—C1—C7	123.8 (2)	C16—C17—H17A	109.8
C2—C1—C7	117.0 (2)	C17A—C17—H17B	109.8
C3—C2—C1	118.2 (2)	C16—C17—H17B	109.8
C3—C2—H2	120.9	H17A—C17—H17B	108.2
C1—C2—H2	120.9	C13A—C17A—C17	125.7 (2)
F3—C3—C2	118.0 (2)	C13A—C17A—S11	113.12 (17)
F3—C3—C4	118.2 (2)	C17—C17A—S11	121.0 (2)
C2—C3—C4	123.7 (2)	C25—C24—H24A	109.2
C5—C4—C3	117.3 (2)	C25—C24—H24B	109.2
C5—C4—H4	121.3	H24A—C24—H24B	107.9
C3—C4—H4	121.3	C26—C25—C24	111.9 (8)
C4—C5—C6	120.6 (2)	C26—C25—H25A	109.2
C4—C5—H5	119.7	C24—C25—H25A	109.2
C6—C5—H5	119.7	C26—C25—H25B	109.2
C1—C6—C5	121.0 (2)	C24—C25—H25B	109.2
C1—C6—H6	119.5	H25A—C25—H25B	107.9
C5—C6—H6	119.5	C25—C26—C27	109.2 (9)
C7—N1—C12	124.59 (19)	C25—C26—H26A	109.8
C7—N1—H1	117.7	C27—C26—H26A	109.8
C12—N1—H1	117.7	C25—C26—H26B	109.8
C12—S11—C17A	90.94 (11)	C27—C26—H26B	109.8
N1—C12—C13	124.67 (19)	H26A—C26—H26B	108.3
N1—C12—S11	122.51 (17)	C26—C27—H27A	110.2
C13—C12—S11	112.82 (16)	C26—C27—H27B	110.2
C12—C13—C13A	111.11 (19)	H27A—C27—H27B	108.5
C12—C13—C37	120.50 (18)	O37—C37—C13	121.6 (2)
C13A—C13—C37	128.3 (2)	O37—C37—C31	116.7 (2)
C17A—C13A—C13	112.0 (2)	C13—C37—C31	121.72 (19)
C17A—C13A—C14	121.3 (2)	C32—C31—C36	118.8 (2)
C13—C13A—C14	126.7 (2)	C32—C31—C37	119.4 (2)
C13A—C14—C15	111.0 (3)	C36—C31—C37	121.6 (2)
C13A—C14—H14A	109.4	C31—C32—C33	120.1 (3)
C15—C14—H14A	109.4	C31—C32—H32	119.9
C13A—C14—H14B	109.4	C33—C32—H32	119.9
C15—C14—H14B	109.4	C34—C33—C32	119.9 (3)
H14A—C14—H14B	108.0	C34—C33—H33	120.0
C16—C15—C14	109.4 (4)	C32—C33—H33	120.0
C16—C15—H15A	109.8	C35—C34—C33	120.7 (3)
C14—C15—H15A	109.8	C35—C34—H34	119.6
C16—C15—H15B	109.8	C33—C34—H34	119.6
C14—C15—H15B	109.8	C34—C35—C36	119.7 (3)
H15A—C15—H15B	108.2	C34—C35—H35	120.1
C15—C16—C17	110.9 (5)	C36—C35—H35	120.1
C15—C16—H16A	109.5	C35—C36—C31	120.6 (3)
C17—C16—H16A	109.5	C35—C36—H36	119.7
C15—C16—H16B	109.5	C31—C36—H36	119.7

O7—C7—C1—C6	−155.4 (2)	C13—C13A—C14—C15	157.6 (4)
N1—C7—C1—C6	24.6 (3)	C13A—C14—C15—C16	50.1 (9)
O7—C7—C1—C2	21.3 (3)	C14—C15—C16—C17	−65.8 (9)
N1—C7—C1—C2	−158.70 (19)	C15—C16—C17—C17A	45.8 (10)
C6—C1—C2—C3	−1.8 (3)	C13—C13A—C17A—C17	−176.0 (6)
C7—C1—C2—C3	−178.6 (2)	C14—C13A—C17A—C17	1.1 (9)
C1—C2—C3—F3	−179.54 (19)	C13—C13A—C17A—S11	−1.1 (2)
C1—C2—C3—C4	1.5 (4)	C14—C13A—C17A—S11	176.0 (5)
F3—C3—C4—C5	−179.1 (2)	C16—C17—C17A—C13A	−14.3 (11)
C2—C3—C4—C5	−0.1 (4)	C16—C17—C17A—S11	171.1 (4)
C3—C4—C5—C6	−0.9 (4)	C12—S11—C17A—C13A	−0.08 (18)
C2—C1—C6—C5	0.8 (3)	C12—S11—C17A—C17	175.1 (6)
C7—C1—C6—C5	177.4 (2)	C24—C25—C26—C27	64.7 (15)
C4—C5—C6—C1	0.6 (4)	C12—C13—C37—O37	13.2 (3)
O7—C7—N1—C12	−0.4 (3)	C13A—C13—C37—O37	−164.1 (2)
C1—C7—N1—C12	179.60 (18)	C12—C13—C37—C31	−166.0 (2)
C7—N1—C12—C13	−179.27 (19)	C13A—C13—C37—C31	16.7 (3)
C7—N1—C12—S11	0.0 (3)	O37—C37—C31—C32	48.4 (3)
C17A—S11—C12—N1	−178.05 (17)	C13—C37—C31—C32	−132.4 (2)
C17A—S11—C12—C13	1.32 (16)	O37—C37—C31—C36	−125.9 (2)
N1—C12—C13—C13A	177.20 (17)	C13—C37—C31—C36	53.4 (3)
S11—C12—C13—C13A	−2.2 (2)	C36—C31—C32—C33	−1.0 (4)
N1—C12—C13—C37	−0.5 (3)	C37—C31—C32—C33	−175.5 (3)
S11—C12—C13—C37	−179.90 (16)	C31—C32—C33—C34	0.8 (5)
C12—C13—C13A—C17A	2.1 (3)	C32—C33—C34—C35	0.1 (6)
C37—C13—C13A—C17A	179.6 (2)	C33—C34—C35—C36	−0.7 (5)
C12—C13—C13A—C14	−174.8 (5)	C34—C35—C36—C31	0.5 (4)
C37—C13—C13A—C14	2.7 (6)	C32—C31—C36—C35	0.4 (4)
C17A—C13A—C14—C15	−19.0 (9)	C37—C31—C36—C35	174.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O37	0.86	2.01	2.650 (3)	130

N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-chlorobenzamide (II) top

Crystal data top

C₂₂H₁₈ClNO₂S	F(000) = 824
M_r = 395.88	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.6776 (6) Å	Cell parameters from 3743 reflections
b = 14.2461 (8) Å	θ = 2.3–25.9°
c = 12.2957 (7) Å	µ = 0.32 mm⁻¹
β = 109.336 (2)°	T = 296 K
V = 1930.13 (18) Å³	Block, colourless
Z = 4	0.25 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	2127 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	R_int = 0.047
φ and ω scans	θ_max = 25.9°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −13→14
T_min = 0.882, T_max = 0.937	k = −17→17
28361 measured reflections	l = −14→15
3743 independent reflections

Refinement top

Refinement on F²	12 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0477P)² + 1.4106P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3743 reflections	Δρ_max = 0.30 e Å⁻³
257 parameters	Δρ_min = −0.28 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C7	0.3052 (3)	0.1590 (2)	0.3054 (3)	0.0537 (8)
O7	0.32402 (18)	0.07451 (16)	0.3102 (2)	0.0725 (7)
C1	0.1822 (2)	0.1999 (2)	0.2546 (2)	0.0489 (7)
C2	0.0837 (3)	0.1403 (2)	0.2274 (3)	0.0650 (9)
H2	0.0960	0.0763	0.2420	0.078*
C3	−0.0329 (3)	0.1740 (2)	0.1790 (3)	0.0677 (9)
H3	−0.0988	0.1333	0.1613	0.081*
C4	−0.0506 (3)	0.2678 (2)	0.1575 (3)	0.0594 (8)
Cl4	−0.19694 (8)	0.31045 (8)	0.09347 (9)	0.0892 (4)
C5	0.0452 (3)	0.3286 (2)	0.1820 (3)	0.0653 (9)
H5	0.0321	0.3924	0.1663	0.078*
C6	0.1611 (3)	0.2943 (2)	0.2301 (3)	0.0623 (9)
H6	0.2265	0.3354	0.2466	0.075*
N1	0.39838 (19)	0.22082 (17)	0.3469 (2)	0.0533 (6)
H1	0.3796	0.2793	0.3453	0.064*
S11	0.57075 (7)	0.08612 (6)	0.41343 (8)	0.0635 (3)
C12	0.5191 (2)	0.1988 (2)	0.3909 (2)	0.0490 (7)
C13	0.6120 (2)	0.2646 (2)	0.4221 (3)	0.0494 (7)
C13A	0.7289 (2)	0.2195 (2)	0.4669 (3)	0.0508 (7)	0.645 (7)
C14	0.8512 (4)	0.2670 (4)	0.512 (2)	0.0704 (12)	0.645 (7)
H14A	0.8458	0.3215	0.5569	0.084*	0.645 (7)
H14B	0.8748	0.2883	0.4470	0.084*	0.645 (7)
C15	0.9492 (4)	0.1985 (4)	0.5870 (6)	0.073 (2)	0.645 (7)
H15A	1.0291	0.2258	0.6030	0.088*	0.645 (7)
H15B	0.9359	0.1881	0.6599	0.088*	0.645 (7)
C16	0.9424 (5)	0.1075 (5)	0.5256 (8)	0.098 (4)	0.645 (7)
H16A	1.0097	0.0678	0.5684	0.117*	0.645 (7)
H16B	0.9487	0.1187	0.4500	0.117*	0.645 (7)
C17	0.8221 (5)	0.0579 (3)	0.513 (2)	0.0762 (16)	0.645 (7)
H17A	0.8114	0.0051	0.4606	0.091*	0.645 (7)
H17B	0.8232	0.0341	0.5871	0.091*	0.645 (7)
C17A	0.7193 (3)	0.1256 (2)	0.4670 (3)	0.0577 (8)	0.645 (7)
C23A	0.7289 (2)	0.2195 (2)	0.4669 (3)	0.0508 (7)	0.355 (7)
C24	0.8530 (6)	0.2643 (5)	0.517 (4)	0.0704 (12)	0.355 (7)
H24B	0.8638	0.2872	0.5941	0.084*	0.355 (7)
H24A	0.8594	0.3173	0.4699	0.084*	0.355 (7)
C25	0.9537 (7)	0.1911 (8)	0.5217 (11)	0.073 (2)	0.355 (7)
H25A	0.9514	0.1761	0.4441	0.088*	0.355 (7)
H25B	1.0328	0.2174	0.5631	0.088*	0.355 (7)
C26	0.9341 (8)	0.1042 (9)	0.5808 (13)	0.098 (4)	0.355 (7)
H26A	0.9248	0.1201	0.6541	0.117*	0.355 (7)
H26B	1.0036	0.0628	0.5954	0.117*	0.355 (7)
C27	0.8192 (8)	0.0548 (5)	0.503 (4)	0.0762 (16)	0.355 (7)
H27A	0.8335	0.0287	0.4359	0.091*	0.355 (7)
H27B	0.7971	0.0039	0.5448	0.091*	0.355 (7)
C27A	0.7193 (3)	0.1256 (2)	0.4670 (3)	0.0577 (8)	0.355 (7)
C37	0.5843 (3)	0.3642 (2)	0.4080 (3)	0.0572 (8)
O37	0.4800 (2)	0.39474 (16)	0.3860 (3)	0.0874 (8)
C31	0.6826 (2)	0.4328 (2)	0.4160 (3)	0.0512 (7)
C32	0.7229 (3)	0.4937 (3)	0.5060 (3)	0.0753 (10)
H32	0.6887	0.4934	0.5644	0.090*
C33	0.8159 (4)	0.5564 (3)	0.5100 (5)	0.1018 (15)
H33	0.8455	0.5969	0.5724	0.122*
C34	0.8628 (4)	0.5585 (3)	0.4238 (5)	0.0999 (15)
H34	0.9237	0.6013	0.4261	0.120*
C35	0.8222 (4)	0.4993 (4)	0.3349 (4)	0.1031 (15)
H35	0.8550	0.5011	0.2756	0.124*
C36	0.7326 (3)	0.4361 (3)	0.3309 (3)	0.0810 (11)
H36	0.7056	0.3948	0.2690	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0484 (17)	0.058 (2)	0.0569 (19)	−0.0049 (15)	0.0201 (14)	−0.0003 (15)
O7	0.0522 (13)	0.0532 (15)	0.1014 (18)	−0.0018 (10)	0.0109 (12)	0.0012 (12)
C1	0.0429 (16)	0.0499 (18)	0.0536 (17)	−0.0011 (13)	0.0156 (13)	0.0025 (14)
C2	0.0530 (19)	0.057 (2)	0.079 (2)	−0.0055 (15)	0.0133 (16)	0.0044 (17)
C3	0.0455 (18)	0.068 (2)	0.082 (2)	−0.0083 (16)	0.0109 (16)	−0.0026 (19)
C4	0.0462 (17)	0.073 (2)	0.0562 (19)	0.0082 (16)	0.0132 (14)	−0.0036 (17)
Cl4	0.0557 (5)	0.1037 (8)	0.0976 (7)	0.0217 (5)	0.0110 (5)	−0.0074 (6)
C5	0.057 (2)	0.060 (2)	0.075 (2)	0.0078 (16)	0.0181 (17)	0.0029 (17)
C6	0.0493 (18)	0.057 (2)	0.077 (2)	−0.0060 (15)	0.0171 (16)	0.0007 (17)
N1	0.0385 (13)	0.0463 (14)	0.0746 (17)	−0.0016 (11)	0.0180 (12)	0.0005 (12)
S11	0.0506 (5)	0.0498 (5)	0.0864 (6)	0.0004 (4)	0.0176 (4)	−0.0018 (4)
C12	0.0434 (15)	0.0482 (17)	0.0576 (18)	−0.0018 (13)	0.0198 (13)	−0.0001 (14)
C13	0.0435 (15)	0.0469 (17)	0.0601 (18)	−0.0009 (13)	0.0204 (13)	0.0003 (14)
C13A	0.0399 (15)	0.0500 (19)	0.0626 (19)	0.0030 (13)	0.0171 (13)	−0.0024 (14)
C14	0.0395 (16)	0.063 (2)	0.100 (3)	0.0026 (15)	0.0122 (17)	−0.005 (2)
C15	0.042 (2)	0.075 (3)	0.093 (6)	0.005 (2)	0.009 (3)	−0.008 (4)
C16	0.058 (3)	0.083 (3)	0.124 (9)	0.028 (2)	−0.007 (4)	−0.031 (5)
C17	0.056 (2)	0.065 (2)	0.097 (4)	0.0137 (17)	0.011 (2)	−0.004 (2)
C17A	0.0476 (17)	0.056 (2)	0.068 (2)	0.0058 (14)	0.0169 (15)	−0.0026 (16)
C23A	0.0399 (15)	0.0500 (19)	0.0626 (19)	0.0030 (13)	0.0171 (13)	−0.0024 (14)
C24	0.0395 (16)	0.063 (2)	0.100 (3)	0.0026 (15)	0.0122 (17)	−0.005 (2)
C25	0.042 (2)	0.075 (3)	0.093 (6)	0.005 (2)	0.009 (3)	−0.008 (4)
C26	0.058 (3)	0.083 (3)	0.124 (9)	0.028 (2)	−0.007 (4)	−0.031 (5)
C27	0.056 (2)	0.065 (2)	0.097 (4)	0.0137 (17)	0.011 (2)	−0.004 (2)
C27A	0.0476 (17)	0.056 (2)	0.068 (2)	0.0058 (14)	0.0169 (15)	−0.0026 (16)
C37	0.0455 (17)	0.0541 (19)	0.071 (2)	0.0009 (14)	0.0181 (15)	−0.0027 (16)
O37	0.0502 (13)	0.0564 (14)	0.155 (2)	0.0055 (11)	0.0335 (14)	−0.0010 (15)
C31	0.0432 (16)	0.0512 (19)	0.0553 (18)	0.0026 (13)	0.0110 (14)	−0.0002 (15)
C32	0.067 (2)	0.083 (3)	0.072 (2)	−0.004 (2)	0.0176 (18)	−0.014 (2)
C33	0.082 (3)	0.077 (3)	0.122 (4)	−0.011 (2)	0.002 (3)	−0.040 (3)
C34	0.061 (3)	0.073 (3)	0.154 (5)	−0.014 (2)	0.020 (3)	0.013 (3)
C35	0.074 (3)	0.133 (4)	0.105 (3)	−0.025 (3)	0.032 (2)	0.024 (3)
C36	0.062 (2)	0.116 (3)	0.067 (2)	−0.022 (2)	0.0238 (19)	−0.009 (2)

Geometric parameters (Å, º) top

C7—O7	1.222 (3)	C16—H16A	0.9700
C7—N1	1.361 (4)	C16—H16B	0.9700
C7—C1	1.483 (4)	C17—C17A	1.497 (5)
C1—C2	1.380 (4)	C17—H17A	0.9700
C1—C6	1.382 (4)	C17—H17B	0.9700
C2—C3	1.379 (4)	C24—C25	1.557 (11)
C2—H2	0.9300	C24—H24B	0.9700
C3—C4	1.364 (4)	C24—H24A	0.9700
C3—H3	0.9300	C25—C26	1.491 (8)
C4—C5	1.367 (4)	C25—H25A	0.9700
C4—Cl4	1.738 (3)	C25—H25B	0.9700
C5—C6	1.375 (4)	C26—C27	1.537 (12)
C5—H5	0.9300	C26—H26A	0.9700
C6—H6	0.9300	C26—H26B	0.9700
N1—C12	1.369 (3)	C27—H27A	0.9700
N1—H1	0.8600	C27—H27B	0.9700
S11—C12	1.705 (3)	C37—O37	1.235 (3)
S11—C17A	1.732 (3)	C37—C31	1.487 (4)
C12—C13	1.388 (4)	C31—C36	1.357 (4)
C13—C13A	1.444 (4)	C31—C32	1.362 (4)
C13—C37	1.452 (4)	C32—C33	1.394 (6)
C13A—C17A	1.343 (4)	C32—H32	0.9300
C13A—C14	1.511 (4)	C33—C34	1.345 (6)
C14—C15	1.556 (11)	C33—H33	0.9300
C14—H14A	0.9700	C34—C35	1.337 (6)
C14—H14B	0.9700	C34—H34	0.9300
C15—C16	1.489 (8)	C35—C36	1.369 (5)
C15—H15A	0.9700	C35—H35	0.9300
C15—H15B	0.9700	C36—H36	0.9300
C16—C17	1.534 (11)

O7—C7—N1	120.7 (3)	C17—C16—H16B	109.6
O7—C7—C1	122.8 (3)	H16A—C16—H16B	108.1
N1—C7—C1	116.5 (3)	C17A—C17—C16	109.5 (6)
C2—C1—C6	118.2 (3)	C17A—C17—H17A	109.8
C2—C1—C7	118.3 (3)	C16—C17—H17A	109.8
C6—C1—C7	123.5 (3)	C17A—C17—H17B	109.8
C3—C2—C1	121.0 (3)	C16—C17—H17B	109.8
C3—C2—H2	119.5	H17A—C17—H17B	108.2
C1—C2—H2	119.5	C13A—C17A—C17	125.8 (3)
C4—C3—C2	119.3 (3)	C13A—C17A—S11	113.4 (2)
C4—C3—H3	120.3	C17—C17A—S11	120.8 (3)
C2—C3—H3	120.3	C25—C24—H24B	109.7
C3—C4—C5	121.2 (3)	C25—C24—H24A	109.7
C3—C4—Cl4	119.5 (3)	H24B—C24—H24A	108.2
C5—C4—Cl4	119.2 (3)	C26—C25—C24	109.8 (11)
C4—C5—C6	119.1 (3)	C26—C25—H25A	109.7
C4—C5—H5	120.5	C24—C25—H25A	109.7
C6—C5—H5	120.5	C26—C25—H25B	109.7
C5—C6—C1	121.3 (3)	C24—C25—H25B	109.7
C5—C6—H6	119.4	H25A—C25—H25B	108.2
C1—C6—H6	119.4	C25—C26—C27	108.7 (12)
C7—N1—C12	126.3 (3)	C25—C26—H26A	109.9
C7—N1—H1	116.9	C27—C26—H26A	109.9
C12—N1—H1	116.9	C25—C26—H26B	109.9
C12—S11—C17A	90.68 (14)	C27—C26—H26B	109.9
N1—C12—C13	124.2 (3)	H26A—C26—H26B	108.3
N1—C12—S11	122.8 (2)	C26—C27—H27A	110.1
C13—C12—S11	112.9 (2)	C26—C27—H27B	110.1
C12—C13—C13A	111.0 (3)	H27A—C27—H27B	108.4
C12—C13—C37	120.3 (2)	O37—C37—C13	122.3 (3)
C13A—C13—C37	128.8 (3)	O37—C37—C31	117.8 (3)
C17A—C13A—C13	112.1 (3)	C13—C37—C31	119.8 (2)
C17A—C13A—C14	121.1 (3)	C36—C31—C32	118.9 (3)
C13—C13A—C14	126.9 (3)	C36—C31—C37	119.5 (3)
C13A—C14—C15	110.8 (6)	C32—C31—C37	121.5 (3)
C13A—C14—H14A	109.5	C31—C32—C33	119.5 (4)
C15—C14—H14A	109.5	C31—C32—H32	120.3
C13A—C14—H14B	109.5	C33—C32—H32	120.3
C15—C14—H14B	109.5	C34—C33—C32	120.2 (4)
H14A—C14—H14B	108.1	C34—C33—H33	119.9
C16—C15—C14	109.8 (9)	C32—C33—H33	119.9
C16—C15—H15A	109.7	C35—C34—C33	120.2 (4)
C14—C15—H15A	109.7	C35—C34—H34	119.9
C16—C15—H15B	109.7	C33—C34—H34	119.9
C14—C15—H15B	109.7	C34—C35—C36	120.3 (4)
H15A—C15—H15B	108.2	C34—C35—H35	119.9
C15—C16—C17	110.3 (10)	C36—C35—H35	119.9
C15—C16—H16A	109.6	C31—C36—C35	120.9 (4)
C17—C16—H16A	109.6	C31—C36—H36	119.5
C15—C16—H16B	109.6	C35—C36—H36	119.5

O7—C7—C1—C2	9.9 (5)	C13—C13A—C14—C15	161.7 (8)
N1—C7—C1—C2	−170.5 (3)	C13A—C14—C15—C16	49 (2)
O7—C7—C1—C6	−168.4 (3)	C14—C15—C16—C17	−66.2 (18)
N1—C7—C1—C6	11.3 (4)	C15—C16—C17—C17A	49 (2)
C6—C1—C2—C3	−1.1 (5)	C13—C13A—C17A—C17	−176.9 (14)
C7—C1—C2—C3	−179.4 (3)	C14—C13A—C17A—C17	2 (2)
C1—C2—C3—C4	0.2 (5)	C13—C13A—C17A—S11	0.1 (4)
C2—C3—C4—C5	0.6 (5)	C14—C13A—C17A—S11	179.4 (13)
C2—C3—C4—Cl4	178.5 (3)	C16—C17—C17A—C13A	−17 (2)
C3—C4—C5—C6	−0.6 (5)	C16—C17—C17A—S11	165.8 (10)
Cl4—C4—C5—C6	−178.5 (2)	C12—S11—C17A—C13A	−0.4 (3)
C4—C5—C6—C1	−0.4 (5)	C12—S11—C17A—C17	176.8 (13)
C2—C1—C6—C5	1.1 (5)	C24—C25—C26—C27	69.1 (18)
C7—C1—C6—C5	179.4 (3)	C12—C13—C37—O37	11.6 (5)
O7—C7—N1—C12	3.7 (5)	C13A—C13—C37—O37	−168.1 (3)
C1—C7—N1—C12	−175.9 (3)	C12—C13—C37—C31	−166.2 (3)
C7—N1—C12—C13	173.6 (3)	C13A—C13—C37—C31	14.2 (5)
C7—N1—C12—S11	−6.6 (4)	O37—C37—C31—C36	−107.6 (4)
C17A—S11—C12—N1	−179.3 (3)	C13—C37—C31—C36	70.2 (4)
C17A—S11—C12—C13	0.6 (2)	O37—C37—C31—C32	71.4 (4)
N1—C12—C13—C13A	179.2 (3)	C13—C37—C31—C32	−110.7 (4)
S11—C12—C13—C13A	−0.6 (3)	C36—C31—C32—C33	−1.3 (5)
N1—C12—C13—C37	−0.5 (5)	C37—C31—C32—C33	179.6 (3)
S11—C12—C13—C37	179.7 (2)	C31—C32—C33—C34	1.9 (6)
C12—C13—C13A—C17A	0.3 (4)	C32—C33—C34—C35	−1.3 (7)
C37—C13—C13A—C17A	180.0 (3)	C33—C34—C35—C36	0.0 (7)
C12—C13—C13A—C14	−179.0 (14)	C32—C31—C36—C35	0.1 (5)
C37—C13—C13A—C14	0.7 (14)	C37—C31—C36—C35	179.1 (3)
C17A—C13A—C14—C15	−17 (2)	C34—C35—C36—C31	0.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O37	0.86	1.99	2.641 (3)	132
C3—H3···Cg1ⁱ	0.93	2.76	3.676 (4)	169
C14—H14A···Cg1	0.97	2.96	3.475 (9)	114
C24—H24A···Cg1	0.97	2.73	3.530 (17)	140

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-difluorobenzamide (III) top

Crystal data top

C₂₂H₁₇F₂NO₂S	Z = 2
M_r = 397.43	F(000) = 412
Triclinic, P1	D_x = 1.383 Mg m⁻³
a = 7.6718 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8833 (3) Å	Cell parameters from 4414 reflections
c = 13.5925 (5) Å	θ = 1.6–27.6°
α = 104.925 (4)°	µ = 0.21 mm⁻¹
β = 95.476 (2)°	T = 296 K
γ = 103.633 (3)°	Block, colourless
V = 954.32 (6) Å³	0.20 × 0.20 × 0.15 mm

Data collection top

Bruker Kappa APEXII diffractometer	2814 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	R_int = 0.041
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −9→9
T_min = 0.942, T_max = 0.970	k = −12→12
21940 measured reflections	l = −17→17
4375 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)] = 0.041	w = 1/[σ²(F_o²) + (0.0379P)² + 0.3345P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.108	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.23 e Å⁻³
4375 reflections	Δρ_min = −0.25 e Å⁻³
267 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
12 restraints	Extinction coefficient: 0.0131 (17)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C7	0.2985 (3)	−0.1093 (2)	0.25624 (16)	0.0428 (5)
O7	0.3232 (2)	−0.18513 (16)	0.17654 (11)	0.0596 (4)
C1	0.3154 (3)	−0.1458 (2)	0.35650 (15)	0.0413 (5)
C2	0.4588 (3)	−0.1956 (2)	0.38729 (17)	0.0513 (5)
F2	0.5870 (2)	−0.20460 (18)	0.32721 (11)	0.0828 (5)
C3	0.4795 (4)	−0.2323 (2)	0.47761 (19)	0.0631 (7)
H3	0.5779	−0.2661	0.4953	0.076*
C4	0.3530 (4)	−0.2184 (2)	0.54089 (18)	0.0645 (7)
H4	0.3657	−0.2426	0.6024	0.077*
C5	0.2073 (4)	−0.1690 (3)	0.51490 (18)	0.0620 (6)
H5	0.1212	−0.1591	0.5581	0.074*
C6	0.1921 (3)	−0.1348 (2)	0.42373 (17)	0.0513 (5)
F6	0.04692 (19)	−0.08836 (18)	0.39741 (12)	0.0821 (5)
N1	0.2570 (2)	0.01864 (17)	0.26251 (12)	0.0430 (4)
H1	0.2418	0.0668	0.3220	0.052*
S11	0.28668 (7)	0.00737 (6)	0.06263 (4)	0.04521 (16)
C12	0.2370 (2)	0.0786 (2)	0.18196 (14)	0.0376 (4)
C13	0.1764 (3)	0.2008 (2)	0.18835 (14)	0.0384 (4)
C13A	0.1798 (3)	0.2408 (2)	0.09357 (15)	0.0408 (5)	0.784 (6)
C14	0.1373 (9)	0.3748 (4)	0.0747 (3)	0.0538 (13)	0.784 (6)
H14A	0.1786	0.4556	0.1373	0.065*	0.784 (6)
H14B	0.0069	0.3567	0.0560	0.065*	0.784 (6)
C15	0.2319 (6)	0.4131 (4)	−0.0120 (3)	0.0719 (13)	0.784 (6)
H15A	0.1923	0.4911	−0.0301	0.086*	0.784 (6)
H15B	0.3624	0.4467	0.0111	0.086*	0.784 (6)
C16	0.1877 (6)	0.2814 (4)	−0.1058 (3)	0.0721 (12)	0.784 (6)
H16A	0.2378	0.3097	−0.1626	0.087*	0.784 (6)
H16B	0.0567	0.2449	−0.1262	0.087*	0.784 (6)
C17	0.2639 (16)	0.1612 (6)	−0.0845 (3)	0.0596 (8)	0.784 (6)
H17B	0.2036	0.0698	−0.1365	0.071*	0.784 (6)
H17A	0.3928	0.1833	−0.0881	0.071*	0.784 (6)
C17A	0.2358 (3)	0.1471 (2)	0.02047 (15)	0.0430 (5)	0.784 (6)
C23A	0.1798 (3)	0.2408 (2)	0.09357 (15)	0.0408 (5)	0.216 (6)
C24	0.178 (4)	0.3878 (13)	0.0789 (10)	0.0538 (13)	0.216 (6)
H24A	0.2917	0.4590	0.1140	0.065*	0.216 (6)
H24B	0.0798	0.4197	0.1091	0.065*	0.216 (6)
C25	0.1530 (18)	0.3780 (16)	−0.0355 (10)	0.0719 (13)	0.216 (6)
H25A	0.0303	0.3209	−0.0678	0.086*	0.216 (6)
H25B	0.1685	0.4749	−0.0431	0.086*	0.216 (6)
C26	0.2875 (19)	0.3092 (14)	−0.0896 (10)	0.0721 (12)	0.216 (6)
H26A	0.4104	0.3637	−0.0558	0.087*	0.216 (6)
H26B	0.2748	0.3122	−0.1606	0.087*	0.216 (6)
C27	0.255 (6)	0.152 (2)	−0.0873 (11)	0.0596 (8)	0.216 (6)
H27A	0.1448	0.0920	−0.1346	0.071*	0.216 (6)
H27B	0.3558	0.1150	−0.1084	0.071*	0.216 (6)
C27A	0.2358 (3)	0.1471 (2)	0.02047 (15)	0.0430 (5)	0.216 (6)
C37	0.1167 (3)	0.2722 (2)	0.28286 (15)	0.0421 (5)
O37	0.1794 (2)	0.26502 (18)	0.36795 (11)	0.0648 (5)
C31	−0.0315 (3)	0.34488 (19)	0.27706 (14)	0.0371 (4)
C32	−0.0286 (3)	0.4664 (2)	0.35635 (16)	0.0496 (5)
H32	0.0702	0.5062	0.4098	0.060*
C33	−0.1713 (3)	0.5282 (2)	0.35617 (19)	0.0594 (6)
H33	−0.1680	0.6106	0.4090	0.071*
C34	−0.3193 (3)	0.4684 (2)	0.27803 (19)	0.0564 (6)
H34	−0.4159	0.5103	0.2784	0.068*
C35	−0.3245 (3)	0.3475 (2)	0.19989 (17)	0.0506 (5)
H35	−0.4252	0.3066	0.1476	0.061*
C36	−0.1803 (3)	0.2864 (2)	0.19885 (15)	0.0436 (5)
H36	−0.1833	0.2052	0.1451	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0445 (12)	0.0452 (11)	0.0463 (12)	0.0214 (9)	0.0107 (9)	0.0168 (9)
O7	0.0837 (12)	0.0613 (9)	0.0483 (9)	0.0418 (9)	0.0203 (8)	0.0172 (7)
C1	0.0490 (12)	0.0376 (10)	0.0434 (11)	0.0190 (9)	0.0079 (9)	0.0157 (9)
C2	0.0582 (14)	0.0505 (12)	0.0540 (13)	0.0283 (11)	0.0099 (11)	0.0175 (10)
F2	0.0810 (10)	0.1194 (12)	0.0805 (10)	0.0712 (10)	0.0281 (8)	0.0394 (9)
C3	0.0720 (17)	0.0602 (14)	0.0618 (15)	0.0279 (13)	−0.0077 (13)	0.0234 (12)
C4	0.0820 (19)	0.0572 (14)	0.0531 (14)	0.0079 (13)	−0.0050 (13)	0.0299 (12)
C5	0.0734 (17)	0.0640 (15)	0.0552 (14)	0.0138 (13)	0.0207 (12)	0.0295 (12)
C6	0.0539 (13)	0.0525 (12)	0.0583 (14)	0.0219 (11)	0.0134 (11)	0.0263 (11)
F6	0.0696 (10)	0.1271 (13)	0.0931 (11)	0.0595 (9)	0.0414 (8)	0.0669 (10)
N1	0.0573 (11)	0.0476 (9)	0.0354 (9)	0.0285 (8)	0.0115 (8)	0.0170 (7)
S11	0.0528 (3)	0.0506 (3)	0.0391 (3)	0.0232 (2)	0.0131 (2)	0.0146 (2)
C12	0.0373 (11)	0.0435 (10)	0.0367 (10)	0.0169 (9)	0.0073 (8)	0.0141 (8)
C13	0.0380 (11)	0.0447 (10)	0.0382 (10)	0.0184 (9)	0.0061 (8)	0.0149 (8)
C13A	0.0361 (11)	0.0501 (11)	0.0436 (11)	0.0159 (9)	0.0073 (9)	0.0219 (9)
C14	0.055 (3)	0.0614 (15)	0.0632 (15)	0.0265 (17)	0.0151 (16)	0.0373 (13)
C15	0.065 (3)	0.084 (3)	0.105 (3)	0.036 (2)	0.044 (2)	0.068 (2)
C16	0.073 (3)	0.104 (3)	0.064 (2)	0.032 (3)	0.022 (2)	0.056 (2)
C17	0.0620 (18)	0.0813 (19)	0.0489 (13)	0.0252 (15)	0.0207 (12)	0.0327 (13)
C17A	0.0385 (11)	0.0563 (12)	0.0405 (11)	0.0157 (9)	0.0079 (9)	0.0219 (10)
C23A	0.0361 (11)	0.0501 (11)	0.0436 (11)	0.0159 (9)	0.0073 (9)	0.0219 (9)
C24	0.055 (3)	0.0614 (15)	0.0632 (15)	0.0265 (17)	0.0151 (16)	0.0373 (13)
C25	0.065 (3)	0.084 (3)	0.105 (3)	0.036 (2)	0.044 (2)	0.068 (2)
C26	0.073 (3)	0.104 (3)	0.064 (2)	0.032 (3)	0.022 (2)	0.056 (2)
C27	0.0620 (18)	0.0813 (19)	0.0489 (13)	0.0252 (15)	0.0207 (12)	0.0327 (13)
C27A	0.0385 (11)	0.0563 (12)	0.0405 (11)	0.0157 (9)	0.0079 (9)	0.0219 (10)
C37	0.0500 (12)	0.0421 (10)	0.0392 (11)	0.0202 (9)	0.0072 (9)	0.0134 (9)
O37	0.0888 (12)	0.0849 (11)	0.0370 (8)	0.0588 (10)	0.0047 (8)	0.0159 (8)
C31	0.0431 (11)	0.0380 (10)	0.0362 (10)	0.0169 (9)	0.0086 (9)	0.0152 (8)
C32	0.0544 (13)	0.0453 (11)	0.0471 (12)	0.0201 (10)	0.0033 (10)	0.0059 (9)
C33	0.0646 (15)	0.0453 (12)	0.0690 (16)	0.0276 (11)	0.0132 (13)	0.0052 (11)
C34	0.0506 (14)	0.0554 (13)	0.0777 (17)	0.0304 (11)	0.0192 (12)	0.0267 (12)
C35	0.0402 (12)	0.0583 (13)	0.0568 (13)	0.0155 (10)	0.0026 (10)	0.0226 (11)
C36	0.0492 (12)	0.0427 (11)	0.0394 (11)	0.0169 (9)	0.0060 (9)	0.0093 (9)

Geometric parameters (Å, º) top

C7—O7	1.208 (2)	C16—H16A	0.9700
C7—N1	1.359 (2)	C16—H16B	0.9700
C7—C1	1.499 (3)	C17—C17A	1.499 (3)
C1—C2	1.379 (3)	C17—H17B	0.9700
C1—C6	1.380 (3)	C17—H17A	0.9700
C2—F2	1.341 (2)	C24—C25	1.522 (6)
C2—C3	1.373 (3)	C24—H24A	0.9700
C3—C4	1.365 (3)	C24—H24B	0.9700
C3—H3	0.9300	C25—C26	1.512 (6)
C4—C5	1.372 (3)	C25—H25A	0.9700
C4—H4	0.9300	C25—H25B	0.9700
C5—C6	1.368 (3)	C26—C27	1.523 (7)
C5—H5	0.9300	C26—H26A	0.9700
C6—F6	1.353 (2)	C26—H26B	0.9700
N1—C12	1.385 (2)	C27—H27A	0.9700
N1—H1	0.8600	C27—H27B	0.9700
S11—C12	1.7111 (19)	C37—O37	1.236 (2)
S11—C17A	1.7338 (19)	C37—C31	1.487 (3)
C12—C13	1.379 (2)	C31—C36	1.381 (3)
C13—C13A	1.443 (3)	C31—C32	1.386 (3)
C13—C37	1.468 (3)	C32—C33	1.374 (3)
C13A—C17A	1.351 (3)	C32—H32	0.9300
C13A—C14	1.513 (3)	C33—C34	1.377 (3)
C14—C15	1.525 (4)	C33—H33	0.9300
C14—H14A	0.9700	C34—C35	1.369 (3)
C14—H14B	0.9700	C34—H34	0.9300
C15—C16	1.513 (4)	C35—C36	1.379 (3)
C15—H15A	0.9700	C35—H35	0.9300
C15—H15B	0.9700	C36—H36	0.9300
C16—C17	1.520 (6)

O7—C7—N1	122.35 (18)	C17—C16—H16B	109.3
O7—C7—C1	123.19 (17)	H16A—C16—H16B	107.9
N1—C7—C1	114.45 (17)	C17A—C17—C16	110.1 (3)
C2—C1—C6	114.98 (18)	C17A—C17—H17B	109.6
C2—C1—C7	120.96 (18)	C16—C17—H17B	109.6
C6—C1—C7	124.06 (18)	C17A—C17—H17A	109.6
F2—C2—C3	118.5 (2)	C16—C17—H17A	109.6
F2—C2—C1	118.20 (18)	H17B—C17—H17A	108.1
C3—C2—C1	123.3 (2)	C13A—C17A—C17	125.9 (2)
C4—C3—C2	118.7 (2)	C13A—C17A—S11	112.59 (14)
C4—C3—H3	120.6	C17—C17A—S11	121.4 (2)
C2—C3—H3	120.6	C25—C24—H24A	109.6
C3—C4—C5	120.9 (2)	C25—C24—H24B	109.6
C3—C4—H4	119.6	H24A—C24—H24B	108.1
C5—C4—H4	119.6	C26—C25—C24	111.7 (7)
C6—C5—C4	118.1 (2)	C26—C25—H25A	109.3
C6—C5—H5	120.9	C24—C25—H25A	109.3
C4—C5—H5	120.9	C26—C25—H25B	109.3
F6—C6—C5	118.1 (2)	C24—C25—H25B	109.3
F6—C6—C1	117.93 (18)	H25A—C25—H25B	107.9
C5—C6—C1	124.0 (2)	C25—C26—C27	110.3 (8)
C7—N1—C12	126.00 (16)	C25—C26—H26A	109.6
C7—N1—H1	117.0	C27—C26—H26A	109.6
C12—N1—H1	117.0	C25—C26—H26B	109.6
C12—S11—C17A	91.04 (9)	C27—C26—H26B	109.6
C13—C12—N1	124.46 (17)	H26A—C26—H26B	108.1
C13—C12—S11	112.65 (14)	C26—C27—H27A	110.0
N1—C12—S11	122.90 (13)	C26—C27—H27B	110.0
C12—C13—C13A	111.36 (16)	H27A—C27—H27B	108.4
C12—C13—C37	120.60 (16)	O37—C37—C13	120.90 (17)
C13A—C13—C37	128.04 (16)	O37—C37—C31	118.50 (17)
C17A—C13A—C13	112.28 (16)	C13—C37—C31	120.43 (16)
C17A—C13A—C14	121.3 (2)	C36—C31—C32	119.09 (18)
C13—C13A—C14	126.4 (2)	C36—C31—C37	121.26 (17)
C13A—C14—C15	109.7 (3)	C32—C31—C37	119.41 (17)
C13A—C14—H14A	109.7	C33—C32—C31	120.2 (2)
C15—C14—H14A	109.7	C33—C32—H32	119.9
C13A—C14—H14B	109.7	C31—C32—H32	119.9
C15—C14—H14B	109.7	C32—C33—C34	120.2 (2)
H14A—C14—H14B	108.2	C32—C33—H33	119.9
C16—C15—C14	110.2 (4)	C34—C33—H33	119.9
C16—C15—H15A	109.6	C35—C34—C33	120.1 (2)
C14—C15—H15A	109.6	C35—C34—H34	119.9
C16—C15—H15B	109.6	C33—C34—H34	119.9
C14—C15—H15B	109.6	C34—C35—C36	119.9 (2)
H15A—C15—H15B	108.1	C34—C35—H35	120.1
C15—C16—C17	111.7 (4)	C36—C35—H35	120.1
C15—C16—H16A	109.3	C35—C36—C31	120.51 (19)
C17—C16—H16A	109.3	C35—C36—H36	119.7
C15—C16—H16B	109.3	C31—C36—H36	119.7

O7—C7—C1—C2	44.1 (3)	C37—C13—C13A—C14	5.8 (4)
N1—C7—C1—C2	−134.5 (2)	C17A—C13A—C14—C15	−21.2 (6)
O7—C7—C1—C6	−135.1 (2)	C13—C13A—C14—C15	155.4 (3)
N1—C7—C1—C6	46.3 (3)	C13A—C14—C15—C16	52.0 (6)
C6—C1—C2—F2	−177.94 (19)	C14—C15—C16—C17	−65.0 (8)
C7—C1—C2—F2	2.8 (3)	C15—C16—C17—C17A	41.7 (10)
C6—C1—C2—C3	0.2 (3)	C13—C13A—C17A—C17	−176.6 (6)
C7—C1—C2—C3	−179.1 (2)	C14—C13A—C17A—C17	0.4 (8)
F2—C2—C3—C4	177.7 (2)	C13—C13A—C17A—S11	−0.1 (2)
C1—C2—C3—C4	−0.4 (4)	C14—C13A—C17A—S11	177.0 (3)
C2—C3—C4—C5	0.2 (4)	C16—C17—C17A—C13A	−10.4 (11)
C3—C4—C5—C6	0.2 (4)	C16—C17—C17A—S11	173.3 (4)
C4—C5—C6—F6	179.0 (2)	C12—S11—C17A—C13A	−1.37 (16)
C4—C5—C6—C1	−0.5 (4)	C12—S11—C17A—C17	175.4 (6)
C2—C1—C6—F6	−179.17 (19)	C24—C25—C26—C27	64.1 (14)
C7—C1—C6—F6	0.1 (3)	C12—C13—C37—O37	28.0 (3)
C2—C1—C6—C5	0.3 (3)	C13A—C13—C37—O37	−152.8 (2)
C7—C1—C6—C5	179.6 (2)	C12—C13—C37—C31	−147.08 (19)
O7—C7—N1—C12	0.2 (3)	C13A—C13—C37—C31	32.1 (3)
C1—C7—N1—C12	178.76 (18)	O37—C37—C31—C36	−137.2 (2)
C7—N1—C12—C13	172.90 (19)	C13—C37—C31—C36	38.0 (3)
C7—N1—C12—S11	−7.3 (3)	O37—C37—C31—C32	37.0 (3)
C17A—S11—C12—C13	2.51 (16)	C13—C37—C31—C32	−147.78 (19)
C17A—S11—C12—N1	−177.29 (17)	C36—C31—C32—C33	−0.7 (3)
N1—C12—C13—C13A	176.82 (18)	C37—C31—C32—C33	−175.0 (2)
S11—C12—C13—C13A	−3.0 (2)	C31—C32—C33—C34	1.0 (3)
N1—C12—C13—C37	−3.9 (3)	C32—C33—C34—C35	−0.3 (4)
S11—C12—C13—C37	176.34 (15)	C33—C34—C35—C36	−0.7 (3)
C12—C13—C13A—C17A	1.9 (2)	C34—C35—C36—C31	1.0 (3)
C37—C13—C13A—C17A	−177.31 (19)	C32—C31—C36—C35	−0.4 (3)
C12—C13—C13A—C14	−174.9 (4)	C37—C31—C36—C35	173.88 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O37	0.86	2.08	2.718 (2)	130
C3—H3···O37ⁱ	0.93	2.50	3.326 (3)	148
C17—H17A···O7ⁱⁱ	0.97	2.59	3.494 (12)	156
C4—H4···Cg1ⁱⁱⁱ	0.93	2.85	3.635 (2)	143
C35—H35···Cg2^iv	0.93	2.75	3.520 (2)	141

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z; (iii) −x, −y, −z+1; (iv) x−1, y, z.

N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2-methoxybenzamide (IV) top

Crystal data top

C₂₃H₂₁NO₃S	Z = 4
M_r = 391.47	F(000) = 824
Triclinic, P1	D_x = 1.344 Mg m⁻³
a = 8.5129 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.9230 (14) Å	Cell parameters from 8692 reflections
c = 19.031 (2) Å	θ = 1.1–27.4°
α = 96.811 (5)°	µ = 0.19 mm⁻¹
β = 102.665 (6)°	T = 296 K
γ = 105.321 (5)°	Block, colourless
V = 1935.1 (4) Å³	0.20 × 0.15 × 0.15 mm

Data collection top

Bruker Kappa APEXII diffractometer	4159 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	R_int = 0.072
φ and ω scans	θ_max = 26.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −10→10
T_min = 0.935, T_max = 0.972	k = −16→16
37373 measured reflections	l = −23→23
8015 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0707P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
8015 reflections	Δρ_max = 0.23 e Å⁻³
511 parameters	Δρ_min = −0.36 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C17	0.7291 (3)	0.4920 (2)	0.42332 (17)	0.0432 (7)
O17	0.6890 (2)	0.46367 (16)	0.35654 (11)	0.0583 (6)
C11	0.8727 (3)	0.5902 (2)	0.46126 (16)	0.0415 (7)
C12	0.9407 (3)	0.6250 (2)	0.53685 (16)	0.0445 (7)
C13	1.0831 (4)	0.7148 (3)	0.56369 (19)	0.0558 (8)
H13	1.135 (4)	0.735 (2)	0.6153 (16)	0.067*
C14	1.1547 (4)	0.7718 (2)	0.5164 (2)	0.0623 (9)
H14	1.2494	0.8325	0.5350	0.075*
C15	1.0888 (4)	0.7406 (3)	0.4423 (2)	0.0616 (9)
H15	1.1372	0.7799	0.4106	0.074*
C16	0.9503 (4)	0.6504 (2)	0.41536 (17)	0.0520 (8)
H16	0.9066	0.6287	0.3649	0.062*
O12	0.8629 (2)	0.56645 (16)	0.58071 (11)	0.0574 (5)
C18	0.9289 (4)	0.5935 (3)	0.65822 (16)	0.0706 (10)
H18A	1.0436	0.5917	0.6708	0.106*
H18B	0.8624	0.5417	0.6805	0.106*
H18C	0.9253	0.6655	0.6757	0.106*
N11	0.6436 (3)	0.43260 (17)	0.46496 (14)	0.0420 (6)
H11	0.6726	0.4563	0.5115	0.071 (11)*
S111	0.44061 (9)	0.28363 (6)	0.34524 (4)	0.0479 (2)
C112	0.5132 (3)	0.3366 (2)	0.43732 (14)	0.0376 (6)
C113	0.4327 (3)	0.2715 (2)	0.47888 (14)	0.0349 (6)
C13A	0.3002 (3)	0.1774 (2)	0.43310 (14)	0.0366 (6)
C114	0.1737 (3)	0.0934 (2)	0.45662 (15)	0.0465 (7)
H11A	0.1351	0.1293	0.4942	0.056*
H11B	0.2278	0.0429	0.4778	0.056*
C115	0.0235 (4)	0.0303 (3)	0.39350 (16)	0.0585 (8)
H11C	−0.0395	−0.0340	0.4081	0.070*
H11D	−0.0501	0.0754	0.3825	0.070*
C116	0.0732 (4)	−0.0040 (2)	0.32617 (17)	0.0617 (9)
H11E	−0.0271	−0.0467	0.2882	0.074*
H11F	0.1452	−0.0502	0.3368	0.074*
C117	0.1663 (4)	0.0936 (2)	0.29797 (16)	0.0556 (8)
H11G	0.2236	0.0694	0.2634	0.067*
H11H	0.0862	0.1269	0.2728	0.067*
C17A	0.2920 (3)	0.1753 (2)	0.36089 (15)	0.0421 (7)
C137	0.4843 (3)	0.2989 (2)	0.55881 (15)	0.0394 (7)
O137	0.5584 (3)	0.39291 (16)	0.59155 (11)	0.0584 (6)
C131	0.4570 (3)	0.2123 (2)	0.60386 (14)	0.0384 (6)
C132	0.4077 (3)	0.2322 (2)	0.66724 (15)	0.0493 (7)
H132	0.3825	0.2968	0.6791	0.059*
C133	0.3958 (4)	0.1579 (3)	0.71268 (17)	0.0661 (9)
H133	0.3608	0.1717	0.7549	0.079*
C134	0.4347 (4)	0.0635 (3)	0.69670 (19)	0.0676 (10)
H134	0.4270	0.0136	0.7281	0.081*
C135	0.4853 (3)	0.0422 (2)	0.6344 (2)	0.0596 (9)
H135	0.5134	−0.0216	0.6238	0.072*
C136	0.4944 (3)	0.1162 (2)	0.58719 (16)	0.0480 (7)
H136	0.5258	0.1010	0.5442	0.058*
C27	0.6652 (3)	−0.0187 (2)	0.90359 (16)	0.0422 (7)
O27	0.6146 (2)	−0.01895 (17)	0.83797 (11)	0.0642 (6)
C21	0.5718 (3)	−0.1027 (2)	0.93938 (16)	0.0414 (7)
C22	0.6084 (3)	−0.1044 (2)	1.01425 (17)	0.0446 (7)
C23	0.5056 (4)	−0.1841 (3)	1.04075 (19)	0.0615 (9)
H23	0.5293	−0.1847	1.0908	0.074*
C24	0.3689 (4)	−0.2621 (3)	0.9936 (2)	0.0708 (10)
H24	0.3013	−0.3156	1.0119	0.085*
C25	0.3312 (4)	−0.2623 (3)	0.9203 (2)	0.0709 (10)
H25	0.2380	−0.3153	0.8887	0.085*
C26	0.4318 (4)	−0.1833 (2)	0.89307 (18)	0.0584 (8)
H26	0.4059	−0.1838	0.8429	0.070*
O22	0.7458 (2)	−0.02601 (16)	1.05790 (11)	0.0558 (5)
C28	0.7914 (4)	−0.0238 (3)	1.13475 (16)	0.0661 (9)
H28A	0.7028	−0.0121	1.1553	0.099*
H28B	0.8937	0.0344	1.1573	0.099*
H28C	0.8085	−0.0921	1.1435	0.099*
N21	0.8057 (3)	0.05953 (16)	0.94501 (12)	0.0395 (5)
H21	0.8377	0.0567	0.9907	0.047*
S211	0.85579 (9)	0.15549 (6)	0.82917 (4)	0.0450 (2)
C212	0.9009 (3)	0.1431 (2)	0.91981 (14)	0.0361 (6)
C213	1.0392 (3)	0.2265 (2)	0.96251 (14)	0.0345 (6)
C23A	1.1148 (3)	0.2983 (2)	0.91849 (14)	0.0365 (6)
C214	1.2753 (3)	0.3921 (2)	0.94344 (15)	0.0485 (7)
H21A	1.3573	0.3730	0.9795	0.058*
H21B	1.2525	0.4556	0.9667	0.058*
C215	1.3484 (4)	0.4203 (3)	0.87987 (17)	0.0628 (9)
H21C	1.4384	0.4890	0.8958	0.075*
H21D	1.3963	0.3641	0.8642	0.075*
C216	1.2157 (4)	0.4297 (3)	0.81655 (17)	0.0649 (9)
H21E	1.2678	0.4529	0.7783	0.078*
H21F	1.1669	0.4852	0.8326	0.078*
C217	1.0772 (4)	0.3228 (2)	0.78561 (16)	0.0523 (8)
H21G	0.9790	0.3363	0.7559	0.063*
H21H	1.1154	0.2752	0.7544	0.063*
C27A	1.0301 (3)	0.2683 (2)	0.84655 (15)	0.0419 (7)
C237	1.0898 (3)	0.2345 (2)	1.04255 (15)	0.0387 (6)
O237	1.0632 (2)	0.15246 (15)	1.07003 (10)	0.0558 (5)
C231	1.1630 (3)	0.3431 (2)	1.09194 (14)	0.0362 (6)
C232	1.2766 (3)	0.3540 (2)	1.15913 (15)	0.0450 (7)
H232	1.3126	0.2949	1.1711	0.054*
C233	1.3360 (4)	0.4516 (3)	1.20796 (16)	0.0550 (8)
H233	1.4131	0.4587	1.2525	0.066*
C234	1.2813 (4)	0.5386 (3)	1.19082 (17)	0.0553 (8)
H234	1.3205	0.6044	1.2241	0.066*
C235	1.1685 (3)	0.5288 (2)	1.12438 (16)	0.0483 (7)
H235	1.1315	0.5878	1.1129	0.058*
C236	1.1106 (3)	0.4314 (2)	1.07503 (14)	0.0407 (7)
H236	1.0356	0.4252	1.0300	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C17	0.0435 (17)	0.0418 (17)	0.049 (2)	0.0131 (14)	0.0166 (15)	0.0177 (15)
O17	0.0615 (13)	0.0640 (14)	0.0417 (13)	0.0025 (11)	0.0148 (10)	0.0154 (11)
C11	0.0411 (16)	0.0343 (16)	0.0530 (19)	0.0115 (13)	0.0162 (14)	0.0161 (14)
C12	0.0451 (17)	0.0414 (17)	0.052 (2)	0.0145 (14)	0.0194 (15)	0.0125 (15)
C13	0.0477 (19)	0.047 (2)	0.068 (2)	0.0107 (16)	0.0124 (17)	0.0033 (18)
C14	0.0450 (19)	0.0430 (19)	0.092 (3)	0.0005 (15)	0.0214 (19)	0.0108 (19)
C15	0.054 (2)	0.054 (2)	0.078 (3)	0.0049 (17)	0.0275 (19)	0.0261 (19)
C16	0.0503 (18)	0.0481 (18)	0.061 (2)	0.0100 (16)	0.0211 (16)	0.0213 (16)
O12	0.0589 (13)	0.0593 (13)	0.0435 (13)	0.0011 (11)	0.0131 (10)	0.0079 (11)
C18	0.071 (2)	0.085 (3)	0.047 (2)	0.010 (2)	0.0170 (18)	0.0030 (19)
N11	0.0439 (14)	0.0374 (13)	0.0422 (16)	0.0061 (11)	0.0118 (11)	0.0104 (12)
S111	0.0529 (5)	0.0507 (5)	0.0370 (4)	0.0070 (4)	0.0127 (3)	0.0135 (4)
C112	0.0342 (15)	0.0396 (16)	0.0397 (16)	0.0116 (13)	0.0093 (12)	0.0102 (13)
C113	0.0368 (15)	0.0321 (15)	0.0353 (16)	0.0077 (12)	0.0108 (12)	0.0080 (13)
C13A	0.0391 (15)	0.0356 (15)	0.0380 (17)	0.0122 (13)	0.0130 (13)	0.0100 (13)
C114	0.0429 (17)	0.0464 (17)	0.0443 (18)	0.0028 (14)	0.0135 (14)	0.0066 (14)
C115	0.0527 (19)	0.058 (2)	0.052 (2)	−0.0011 (16)	0.0125 (16)	0.0047 (16)
C116	0.057 (2)	0.057 (2)	0.056 (2)	−0.0008 (16)	0.0158 (17)	−0.0027 (17)
C117	0.060 (2)	0.0520 (19)	0.0429 (19)	0.0054 (16)	0.0075 (15)	0.0019 (15)
C17A	0.0444 (16)	0.0386 (16)	0.0397 (17)	0.0085 (13)	0.0096 (13)	0.0059 (13)
C137	0.0434 (16)	0.0387 (17)	0.0368 (17)	0.0107 (14)	0.0142 (13)	0.0069 (14)
O137	0.0811 (15)	0.0413 (13)	0.0447 (13)	0.0050 (11)	0.0188 (11)	0.0035 (10)
C131	0.0362 (15)	0.0428 (17)	0.0309 (16)	0.0054 (13)	0.0061 (12)	0.0062 (13)
C132	0.0522 (18)	0.0560 (19)	0.0365 (17)	0.0099 (15)	0.0125 (14)	0.0096 (15)
C133	0.061 (2)	0.083 (3)	0.042 (2)	0.001 (2)	0.0105 (16)	0.0200 (19)
C134	0.058 (2)	0.078 (3)	0.053 (2)	−0.0005 (19)	−0.0025 (17)	0.037 (2)
C135	0.0419 (18)	0.050 (2)	0.082 (3)	0.0113 (15)	0.0009 (17)	0.0280 (19)
C136	0.0420 (17)	0.0532 (19)	0.0469 (18)	0.0117 (14)	0.0095 (14)	0.0114 (16)
C27	0.0414 (17)	0.0390 (17)	0.0436 (19)	0.0108 (14)	0.0077 (14)	0.0070 (14)
O27	0.0591 (13)	0.0657 (15)	0.0460 (14)	−0.0058 (11)	−0.0010 (11)	0.0110 (11)
C21	0.0379 (16)	0.0377 (16)	0.0511 (19)	0.0125 (13)	0.0135 (14)	0.0115 (14)
C22	0.0424 (17)	0.0389 (17)	0.059 (2)	0.0167 (14)	0.0171 (15)	0.0156 (15)
C23	0.062 (2)	0.055 (2)	0.080 (3)	0.0189 (18)	0.0327 (19)	0.0316 (19)
C24	0.059 (2)	0.050 (2)	0.108 (3)	0.0067 (18)	0.037 (2)	0.026 (2)
C25	0.053 (2)	0.047 (2)	0.100 (3)	−0.0028 (16)	0.018 (2)	0.009 (2)
C26	0.0520 (19)	0.0461 (19)	0.066 (2)	0.0068 (16)	0.0067 (17)	0.0024 (17)
O22	0.0563 (13)	0.0579 (13)	0.0445 (13)	0.0027 (11)	0.0089 (10)	0.0170 (10)
C28	0.071 (2)	0.086 (3)	0.044 (2)	0.0231 (19)	0.0141 (17)	0.0247 (18)
N21	0.0408 (13)	0.0384 (13)	0.0355 (13)	0.0070 (11)	0.0073 (11)	0.0087 (11)
S211	0.0495 (4)	0.0447 (4)	0.0367 (4)	0.0085 (4)	0.0105 (3)	0.0063 (3)
C212	0.0388 (15)	0.0351 (15)	0.0373 (16)	0.0123 (13)	0.0130 (13)	0.0088 (13)
C213	0.0376 (15)	0.0305 (15)	0.0351 (16)	0.0108 (12)	0.0089 (12)	0.0051 (12)
C23A	0.0398 (15)	0.0326 (15)	0.0379 (17)	0.0109 (13)	0.0129 (13)	0.0040 (13)
C214	0.0449 (17)	0.0453 (18)	0.0529 (19)	0.0067 (14)	0.0170 (15)	0.0075 (15)
C215	0.057 (2)	0.064 (2)	0.062 (2)	−0.0002 (17)	0.0284 (18)	0.0125 (18)
C216	0.071 (2)	0.062 (2)	0.062 (2)	0.0062 (19)	0.0299 (19)	0.0231 (18)
C217	0.063 (2)	0.0466 (18)	0.051 (2)	0.0134 (16)	0.0260 (16)	0.0122 (15)
C27A	0.0472 (16)	0.0396 (16)	0.0423 (18)	0.0144 (14)	0.0174 (14)	0.0065 (14)
C237	0.0365 (15)	0.0385 (16)	0.0418 (17)	0.0121 (13)	0.0093 (13)	0.0099 (14)
O237	0.0694 (14)	0.0410 (12)	0.0494 (13)	0.0107 (10)	0.0034 (10)	0.0160 (10)
C231	0.0350 (15)	0.0392 (16)	0.0338 (16)	0.0077 (12)	0.0107 (12)	0.0096 (13)
C232	0.0474 (17)	0.0466 (18)	0.0383 (17)	0.0097 (14)	0.0074 (14)	0.0141 (15)
C233	0.0528 (19)	0.066 (2)	0.0354 (18)	0.0049 (17)	0.0058 (14)	0.0090 (16)
C234	0.060 (2)	0.0483 (19)	0.049 (2)	0.0040 (16)	0.0181 (16)	−0.0013 (16)
C235	0.0531 (18)	0.0462 (18)	0.0510 (19)	0.0199 (15)	0.0192 (15)	0.0085 (16)
C236	0.0438 (16)	0.0439 (17)	0.0355 (16)	0.0152 (14)	0.0098 (13)	0.0087 (14)

Geometric parameters (Å, º) top

C17—O17	1.224 (3)	C27—O27	1.228 (3)
C17—N11	1.360 (3)	C27—N21	1.354 (3)
C17—C11	1.484 (4)	C27—C21	1.493 (4)
C11—C16	1.395 (4)	C21—C22	1.395 (4)
C11—C12	1.397 (4)	C21—C26	1.396 (4)
C12—O12	1.355 (3)	C22—O22	1.354 (3)
C12—C13	1.386 (4)	C22—C23	1.386 (4)
C13—C14	1.374 (4)	C23—C24	1.372 (4)
C13—H13	0.96 (3)	C23—H23	0.9300
C14—C15	1.364 (4)	C24—C25	1.361 (5)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.370 (4)	C25—C26	1.379 (4)
C15—H15	0.9300	C25—H25	0.9300
C16—H16	0.9300	C26—H26	0.9300
O12—C18	1.423 (3)	O22—C28	1.423 (3)
C18—H18A	0.9600	C28—H28A	0.9600
C18—H18B	0.9600	C28—H28B	0.9600
C18—H18C	0.9600	C28—H28C	0.9600
N11—C112	1.382 (3)	N21—C212	1.373 (3)
N11—H11	0.8600	N21—H21	0.8600
S111—C112	1.714 (3)	S211—C212	1.720 (3)
S111—C17A	1.725 (3)	S211—C27A	1.722 (3)
C112—C113	1.376 (3)	C212—C213	1.382 (3)
C113—C13A	1.451 (3)	C213—C23A	1.444 (3)
C113—C137	1.459 (3)	C213—C237	1.472 (3)
C13A—C17A	1.357 (3)	C23A—C27A	1.356 (3)
C13A—C114	1.498 (3)	C23A—C214	1.505 (4)
C114—C115	1.512 (4)	C214—C215	1.516 (4)
C114—H11A	0.9700	C214—H21A	0.9700
C114—H11B	0.9700	C214—H21B	0.9700
C115—C116	1.490 (4)	C215—C216	1.501 (4)
C115—H11C	0.9700	C215—H21C	0.9700
C115—H11D	0.9700	C215—H21D	0.9700
C116—C117	1.525 (4)	C216—C217	1.512 (4)
C116—H11E	0.9700	C216—H21E	0.9700
C116—H11F	0.9700	C216—H21F	0.9700
C117—C17A	1.495 (4)	C217—C27A	1.500 (4)
C117—H11G	0.9700	C217—H21G	0.9700
C117—H11H	0.9700	C217—H21H	0.9700
C137—O137	1.227 (3)	C237—O237	1.227 (3)
C137—C131	1.489 (4)	C237—C231	1.486 (3)
C131—C132	1.379 (4)	C231—C236	1.378 (3)
C131—C136	1.380 (4)	C231—C232	1.390 (3)
C132—C133	1.366 (4)	C232—C233	1.374 (4)
C132—H132	0.9300	C232—H232	0.9300
C133—C134	1.363 (4)	C233—C234	1.373 (4)
C133—H133	0.9300	C233—H233	0.9300
C134—C135	1.370 (4)	C234—C235	1.379 (4)
C134—H134	0.9300	C234—H234	0.9300
C135—C136	1.385 (4)	C235—C236	1.378 (4)
C135—H135	0.9300	C235—H235	0.9300
C136—H136	0.9300	C236—H236	0.9300

O17—C17—N11	120.3 (3)	O27—C27—N21	120.1 (3)
O17—C17—C11	121.5 (3)	O27—C27—C21	121.0 (3)
N11—C17—C11	118.1 (3)	N21—C27—C21	118.9 (3)
C16—C11—C12	117.7 (3)	C22—C21—C26	118.1 (3)
C16—C11—C17	115.3 (3)	C22—C21—C27	125.8 (3)
C12—C11—C17	126.9 (3)	C26—C21—C27	116.0 (3)
O12—C12—C13	123.1 (3)	O22—C22—C23	123.1 (3)
O12—C12—C11	117.0 (2)	O22—C22—C21	117.0 (2)
C13—C12—C11	119.9 (3)	C23—C22—C21	119.9 (3)
C14—C13—C12	120.3 (3)	C24—C23—C22	120.3 (3)
C14—C13—H13	119.6 (18)	C24—C23—H23	119.8
C12—C13—H13	120.0 (18)	C22—C23—H23	119.8
C15—C14—C13	120.8 (3)	C25—C24—C23	120.8 (3)
C15—C14—H14	119.6	C25—C24—H24	119.6
C13—C14—H14	119.6	C23—C24—H24	119.6
C14—C15—C16	119.2 (3)	C24—C25—C26	119.6 (3)
C14—C15—H15	120.4	C24—C25—H25	120.2
C16—C15—H15	120.4	C26—C25—H25	120.2
C15—C16—C11	122.1 (3)	C25—C26—C21	121.2 (3)
C15—C16—H16	119.0	C25—C26—H26	119.4
C11—C16—H16	119.0	C21—C26—H26	119.4
C12—O12—C18	120.5 (2)	C22—O22—C28	119.9 (2)
O12—C18—H18A	109.5	O22—C28—H28A	109.5
O12—C18—H18B	109.5	O22—C28—H28B	109.5
H18A—C18—H18B	109.5	H28A—C28—H28B	109.5
O12—C18—H18C	109.5	O22—C28—H28C	109.5
H18A—C18—H18C	109.5	H28A—C28—H28C	109.5
H18B—C18—H18C	109.5	H28B—C28—H28C	109.5
C17—N11—C112	124.3 (2)	C27—N21—C212	125.1 (2)
C17—N11—H11	117.9	C27—N21—H21	117.5
C112—N11—H11	117.9	C212—N21—H21	117.5
C112—S111—C17A	90.94 (13)	C212—S211—C27A	91.15 (13)
C113—C112—N11	125.1 (2)	N21—C212—C213	125.4 (2)
C113—C112—S111	112.8 (2)	N21—C212—S211	122.28 (19)
N11—C112—S111	122.0 (2)	C213—C212—S211	112.33 (19)
C112—C113—C13A	111.4 (2)	C212—C213—C23A	111.3 (2)
C112—C113—C137	121.1 (2)	C212—C213—C237	120.3 (2)
C13A—C113—C137	127.5 (2)	C23A—C213—C237	128.4 (2)
C17A—C13A—C113	111.6 (2)	C27A—C23A—C213	112.2 (2)
C17A—C13A—C114	120.5 (2)	C27A—C23A—C214	120.3 (2)
C113—C13A—C114	127.8 (2)	C213—C23A—C214	127.4 (2)
C13A—C114—C115	112.2 (2)	C23A—C214—C215	111.5 (2)
C13A—C114—H11A	109.2	C23A—C214—H21A	109.3
C115—C114—H11A	109.2	C215—C214—H21A	109.3
C13A—C114—H11B	109.2	C23A—C214—H21B	109.3
C115—C114—H11B	109.2	C215—C214—H21B	109.3
H11A—C114—H11B	107.9	H21A—C214—H21B	108.0
C116—C115—C114	112.6 (3)	C216—C215—C214	111.2 (2)
C116—C115—H11C	109.1	C216—C215—H21C	109.4
C114—C115—H11C	109.1	C214—C215—H21C	109.4
C116—C115—H11D	109.1	C216—C215—H21D	109.4
C114—C115—H11D	109.1	C214—C215—H21D	109.4
H11C—C115—H11D	107.8	H21C—C215—H21D	108.0
C115—C116—C117	112.0 (3)	C215—C216—C217	112.1 (3)
C115—C116—H11E	109.2	C215—C216—H21E	109.2
C117—C116—H11E	109.2	C217—C216—H21E	109.2
C115—C116—H11F	109.2	C215—C216—H21F	109.2
C117—C116—H11F	109.2	C217—C216—H21F	109.2
H11E—C116—H11F	107.9	H21E—C216—H21F	107.9
C17A—C117—C116	109.6 (2)	C27A—C217—C216	110.3 (2)
C17A—C117—H11G	109.7	C27A—C217—H21G	109.6
C116—C117—H11G	109.7	C216—C217—H21G	109.6
C17A—C117—H11H	109.7	C27A—C217—H21H	109.6
C116—C117—H11H	109.7	C216—C217—H21H	109.6
H11G—C117—H11H	108.2	H21G—C217—H21H	108.1
C13A—C17A—C117	126.4 (3)	C23A—C27A—C217	126.1 (3)
C13A—C17A—S111	113.2 (2)	C23A—C27A—S211	112.9 (2)
C117—C17A—S111	120.3 (2)	C217—C27A—S211	121.0 (2)
O137—C137—C113	121.6 (2)	O237—C237—C213	120.9 (2)
O137—C137—C131	117.3 (2)	O237—C237—C231	118.6 (2)
C113—C137—C131	121.0 (2)	C213—C237—C231	120.4 (2)
C132—C131—C136	119.0 (3)	C236—C231—C232	119.1 (2)
C132—C131—C137	119.4 (2)	C236—C231—C237	121.2 (2)
C136—C131—C137	121.4 (2)	C232—C231—C237	119.5 (2)
C133—C132—C131	120.5 (3)	C233—C232—C231	120.5 (3)
C133—C132—H132	119.7	C233—C232—H232	119.8
C131—C132—H132	119.7	C231—C232—H232	119.8
C134—C133—C132	120.6 (3)	C234—C233—C232	119.9 (3)
C134—C133—H133	119.7	C234—C233—H233	120.1
C132—C133—H133	119.7	C232—C233—H233	120.1
C133—C134—C135	120.1 (3)	C233—C234—C235	120.2 (3)
C133—C134—H134	120.0	C233—C234—H234	119.9
C135—C134—H134	120.0	C235—C234—H234	119.9
C134—C135—C136	119.8 (3)	C236—C235—C234	119.9 (3)
C134—C135—H135	120.1	C236—C235—H235	120.1
C136—C135—H135	120.1	C234—C235—H235	120.1
C131—C136—C135	120.1 (3)	C231—C236—C235	120.5 (3)
C131—C136—H136	119.9	C231—C236—H236	119.8
C135—C136—H136	119.9	C235—C236—H236	119.8

O17—C17—C11—C16	3.8 (4)	O27—C27—C21—C22	−173.8 (3)
N11—C17—C11—C16	−177.2 (2)	N21—C27—C21—C22	5.0 (4)
O17—C17—C11—C12	−173.4 (3)	O27—C27—C21—C26	3.6 (4)
N11—C17—C11—C12	5.6 (4)	N21—C27—C21—C26	−177.7 (2)
C16—C11—C12—O12	179.3 (2)	C26—C21—C22—O22	179.3 (2)
C17—C11—C12—O12	−3.6 (4)	C27—C21—C22—O22	−3.4 (4)
C16—C11—C12—C13	−1.6 (4)	C26—C21—C22—C23	−0.8 (4)
C17—C11—C12—C13	175.5 (3)	C27—C21—C22—C23	176.5 (2)
O12—C12—C13—C14	−179.0 (3)	O22—C22—C23—C24	−179.3 (3)
C11—C12—C13—C14	1.9 (4)	C21—C22—C23—C24	0.8 (4)
C12—C13—C14—C15	−0.8 (5)	C22—C23—C24—C25	−0.5 (5)
C13—C14—C15—C16	−0.6 (5)	C23—C24—C25—C26	0.3 (5)
C14—C15—C16—C11	0.9 (4)	C24—C25—C26—C21	−0.3 (5)
C12—C11—C16—C15	0.2 (4)	C22—C21—C26—C25	0.5 (4)
C17—C11—C16—C15	−177.3 (2)	C27—C21—C26—C25	−177.0 (3)
C13—C12—O12—C18	−2.0 (4)	C23—C22—O22—C28	0.7 (4)
C11—C12—O12—C18	177.1 (2)	C21—C22—O22—C28	−179.3 (2)
O17—C17—N11—C112	2.4 (4)	O27—C27—N21—C212	0.6 (4)
C11—C17—N11—C112	−176.7 (2)	C21—C27—N21—C212	−178.2 (2)
C17—N11—C112—C113	175.4 (2)	C27—N21—C212—C213	176.4 (2)
C17—N11—C112—S111	−1.9 (3)	C27—N21—C212—S211	−2.5 (3)
C17A—S111—C112—C113	2.9 (2)	C27A—S211—C212—N21	−177.5 (2)
C17A—S111—C112—N11	−179.6 (2)	C27A—S211—C212—C213	3.48 (19)
N11—C112—C113—C13A	179.3 (2)	N21—C212—C213—C23A	177.6 (2)
S111—C112—C113—C13A	−3.2 (3)	S211—C212—C213—C23A	−3.4 (3)
N11—C112—C113—C137	−1.6 (4)	N21—C212—C213—C237	−3.5 (4)
S111—C112—C113—C137	175.89 (18)	S211—C212—C213—C237	175.46 (17)
C112—C113—C13A—C17A	1.9 (3)	C212—C213—C23A—C27A	1.4 (3)
C137—C113—C13A—C17A	−177.2 (2)	C237—C213—C23A—C27A	−177.3 (2)
C112—C113—C13A—C114	−173.7 (2)	C212—C213—C23A—C214	−174.1 (2)
C137—C113—C13A—C114	7.3 (4)	C237—C213—C23A—C214	7.1 (4)
C17A—C13A—C114—C115	−13.8 (4)	C27A—C23A—C214—C215	−16.8 (4)
C113—C13A—C114—C115	161.4 (2)	C213—C23A—C214—C215	158.4 (2)
C13A—C114—C115—C116	44.5 (3)	C23A—C214—C215—C216	48.3 (3)
C114—C115—C116—C117	−61.3 (4)	C214—C215—C216—C217	−63.0 (3)
C115—C116—C117—C17A	43.5 (3)	C215—C216—C217—C27A	41.9 (3)
C113—C13A—C17A—C117	−177.0 (2)	C213—C23A—C27A—C217	−178.1 (2)
C114—C13A—C17A—C117	−1.1 (4)	C214—C23A—C27A—C217	−2.1 (4)
C113—C13A—C17A—S111	0.3 (3)	C213—C23A—C27A—S211	1.2 (3)
C114—C13A—C17A—S111	176.23 (19)	C214—C23A—C27A—S211	177.12 (19)
C116—C117—C17A—C13A	−13.7 (4)	C216—C217—C27A—C23A	−10.3 (4)
C116—C117—C17A—S111	169.2 (2)	C216—C217—C27A—S211	170.5 (2)
C112—S111—C17A—C13A	−1.8 (2)	C212—S211—C27A—C23A	−2.7 (2)
C112—S111—C17A—C117	175.7 (2)	C212—S211—C27A—C217	176.7 (2)
C112—C113—C137—O137	23.8 (4)	C212—C213—C237—O237	29.9 (4)
C13A—C113—C137—O137	−157.3 (3)	C23A—C213—C237—O237	−151.4 (2)
C112—C113—C137—C131	−152.9 (2)	C212—C213—C237—C231	−145.6 (2)
C13A—C113—C137—C131	26.1 (4)	C23A—C213—C237—C231	33.0 (4)
O137—C137—C131—C132	42.1 (4)	O237—C237—C231—C236	−141.3 (3)
C113—C137—C131—C132	−141.1 (3)	C213—C237—C231—C236	34.3 (4)
O137—C137—C131—C136	−132.0 (3)	O237—C237—C231—C232	33.6 (4)
C113—C137—C131—C136	44.8 (4)	C213—C237—C231—C232	−150.8 (2)
C136—C131—C132—C133	−0.2 (4)	C236—C231—C232—C233	−0.1 (4)
C137—C131—C132—C133	−174.4 (3)	C237—C231—C232—C233	−175.1 (2)
C131—C132—C133—C134	1.0 (5)	C231—C232—C233—C234	0.9 (4)
C132—C133—C134—C135	−0.4 (5)	C232—C233—C234—C235	−0.8 (4)
C133—C134—C135—C136	−0.9 (5)	C233—C234—C235—C236	−0.1 (4)
C132—C131—C136—C135	−1.2 (4)	C232—C231—C236—C235	−0.7 (4)
C137—C131—C136—C135	173.0 (2)	C237—C231—C236—C235	174.1 (2)
C134—C135—C136—C131	1.7 (4)	C234—C235—C236—C231	0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12	0.86	1.95	2.630 (3)	136
N11—H11···O137	0.86	2.11	2.731 (3)	128
N21—H21···O22	0.86	1.93	2.616 (3)	136
N21—H21···O237	0.86	2.13	2.748 (3)	129
C134—H134···O27	0.93	2.49	3.232 (4)	137
C235—H235···Cg3ⁱ	0.93	2.95	3.869 (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

C₁₅H₁₅NOS	D_x = 1.273 Mg m⁻³
M_r = 257.34	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pna2₁	Cell parameters from 3556 reflections
a = 9.2080 (4) Å	θ = 3.3–28.2°
b = 14.0485 (7) Å	µ = 0.23 mm⁻¹
c = 10.3826 (6) Å	T = 295 K
V = 1343.08 (12) Å³	Block, colourless
Z = 4	0.30 × 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 tube	R_int = 0.021
φ and ω scans	θ_max = 28.2°, θ_min = 3.3°
Absorption correction: multi-scan CrysAlis RED (Agilent, 2012)	h = −11→11
T_min = 0.948, T_max = 0.966	k = −7→17
3556 measured reflections	l = −8→13
1984 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)] = 0.036	w = 1/[σ²(F_o²) + (0.0447P)² + 0.1113P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.086	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.13 e Å⁻³
1984 reflections	Δρ_min = −0.23 e Å⁻³
176 parameters	Absolute structure: Flack x determined using 422 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
13 restraints	Absolute structure parameter: −0.03 (6)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	−0.01074 (7)	0.60683 (5)	0.43072 (12)	0.0549 (2)
C2	0.1557 (3)	0.6376 (2)	0.3673 (3)	0.0439 (7)
C3	0.2490 (3)	0.55885 (19)	0.3594 (3)	0.0377 (6)
C3A	0.1817 (3)	0.47431 (19)	0.4150 (3)	0.0397 (6)	0.887 (9)
C4	0.2556 (5)	0.3800 (4)	0.4395 (11)	0.0546 (9)	0.887 (9)
H4A	0.3549	0.3910	0.4671	0.066*	0.887 (9)
H4B	0.2583	0.3434	0.3604	0.066*	0.887 (9)
C5	0.1742 (4)	0.3240 (3)	0.5432 (6)	0.0645 (15)	0.887 (9)
H5A	0.2120	0.2596	0.5470	0.077*	0.887 (9)
H5B	0.1900	0.3536	0.6265	0.077*	0.887 (9)
C6	0.0132 (4)	0.3210 (3)	0.5147 (6)	0.0682 (16)	0.887 (9)
H6A	−0.0348	0.2788	0.5751	0.082*	0.887 (9)
H6B	−0.0025	0.2966	0.4284	0.082*	0.887 (9)
C7	−0.0508 (5)	0.4208 (4)	0.5257 (10)	0.0624 (10)	0.887 (9)
H7A	−0.1476	0.4218	0.4890	0.075*	0.887 (9)
H7B	−0.0576	0.4390	0.6156	0.075*	0.887 (9)
C7A	0.0453 (3)	0.4895 (2)	0.4549 (3)	0.0458 (7)	0.887 (9)
C23A	0.1817 (3)	0.47431 (19)	0.4150 (3)	0.0397 (6)	0.113 (9)
C24	0.260 (3)	0.383 (2)	0.445 (7)	0.0546 (9)	0.113 (9)
H24A	0.3259	0.3927	0.5170	0.066*	0.113 (9)
H24B	0.3169	0.3630	0.3714	0.066*	0.113 (9)
C25	0.151 (3)	0.3044 (10)	0.480 (3)	0.0645 (15)	0.113 (9)
H25A	0.0994	0.2847	0.4029	0.077*	0.113 (9)
H25B	0.2024	0.2496	0.5138	0.077*	0.113 (9)
C26	0.044 (3)	0.3399 (15)	0.579 (3)	0.0682 (16)	0.113 (9)
H26A	0.0954	0.3645	0.6531	0.082*	0.113 (9)
H26B	−0.0173	0.2876	0.6074	0.082*	0.113 (9)
C27	−0.051 (3)	0.418 (2)	0.521 (7)	0.0624 (10)	0.113 (9)
H27A	−0.1184	0.3909	0.4597	0.075*	0.113 (9)
H27B	−0.1063	0.4492	0.5885	0.075*	0.113 (9)
C27A	0.0453 (3)	0.4895 (2)	0.4549 (3)	0.0458 (7)	0.113 (9)
N2	0.1839 (3)	0.72731 (17)	0.3320 (3)	0.0586 (7)
H2A	0.2674	0.7418	0.3005	0.070*
H2B	0.1185	0.7705	0.3410	0.070*
C37	0.3896 (3)	0.5705 (2)	0.3022 (3)	0.0444 (7)
O37	0.4441 (2)	0.65081 (16)	0.2880 (3)	0.0665 (7)
C31	0.4730 (3)	0.4869 (2)	0.2516 (3)	0.0448 (7)
C32	0.6207 (3)	0.4802 (3)	0.2752 (4)	0.0637 (10)
H32	0.6668	0.5258	0.3256	0.076*
C33	0.6992 (4)	0.4058 (3)	0.2237 (5)	0.0843 (13)
H33	0.7981	0.4007	0.2404	0.101*
C34	0.6313 (5)	0.3388 (3)	0.1474 (5)	0.0834 (13)
H34	0.6842	0.2882	0.1137	0.100*
C35	0.4867 (4)	0.3466 (3)	0.1214 (4)	0.0726 (11)
H35	0.4416	0.3025	0.0679	0.087*
C36	0.4079 (4)	0.4196 (2)	0.1740 (4)	0.0573 (8)
H36	0.3089	0.4239	0.1571	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0484 (3)	0.0496 (4)	0.0667 (5)	0.0123 (3)	0.0063 (4)	0.0006 (5)
C2	0.0470 (15)	0.0387 (15)	0.0459 (16)	−0.0003 (13)	−0.0054 (14)	−0.0016 (14)
C3	0.0396 (13)	0.0323 (13)	0.0411 (15)	0.0012 (12)	−0.0030 (11)	−0.0008 (13)
C3A	0.0426 (11)	0.0355 (13)	0.0409 (16)	0.0002 (11)	0.0000 (13)	0.0013 (14)
C4	0.0520 (14)	0.0404 (16)	0.071 (2)	0.0046 (12)	0.0094 (19)	0.0110 (19)
C5	0.067 (2)	0.051 (2)	0.076 (4)	0.0078 (19)	0.013 (2)	0.024 (2)
C6	0.066 (2)	0.054 (2)	0.084 (4)	−0.0099 (19)	0.019 (2)	0.021 (3)
C7	0.0488 (16)	0.067 (2)	0.071 (2)	0.0030 (16)	0.0158 (16)	0.016 (2)
C7A	0.0434 (12)	0.0446 (16)	0.0494 (19)	0.0010 (11)	0.0033 (14)	0.0052 (15)
C23A	0.0426 (11)	0.0355 (13)	0.0409 (16)	0.0002 (11)	0.0000 (13)	0.0013 (14)
C24	0.0520 (14)	0.0404 (16)	0.071 (2)	0.0046 (12)	0.0094 (19)	0.0110 (19)
C25	0.067 (2)	0.051 (2)	0.076 (4)	0.0078 (19)	0.013 (2)	0.024 (2)
C26	0.066 (2)	0.054 (2)	0.084 (4)	−0.0099 (19)	0.019 (2)	0.021 (3)
C27	0.0488 (16)	0.067 (2)	0.071 (2)	0.0030 (16)	0.0158 (16)	0.016 (2)
C27A	0.0434 (12)	0.0446 (16)	0.0494 (19)	0.0010 (11)	0.0033 (14)	0.0052 (15)
N2	0.0606 (14)	0.0332 (14)	0.082 (2)	0.0061 (12)	0.0000 (14)	0.0055 (15)
C37	0.0420 (13)	0.0399 (16)	0.0514 (17)	−0.0059 (13)	−0.0039 (13)	0.0056 (15)
O37	0.0547 (12)	0.0414 (13)	0.104 (2)	−0.0117 (11)	0.0080 (13)	0.0090 (14)
C31	0.0467 (14)	0.0439 (17)	0.0439 (17)	0.0007 (13)	0.0076 (13)	0.0072 (15)
C32	0.0475 (15)	0.074 (2)	0.070 (3)	0.0010 (16)	0.0045 (16)	0.000 (2)
C33	0.058 (2)	0.099 (3)	0.096 (3)	0.025 (2)	0.021 (2)	0.013 (3)
C34	0.101 (3)	0.071 (3)	0.078 (3)	0.021 (2)	0.038 (3)	−0.002 (2)
C35	0.091 (3)	0.065 (3)	0.062 (2)	0.000 (2)	0.018 (2)	−0.014 (2)
C36	0.0590 (17)	0.059 (2)	0.0542 (19)	−0.0043 (16)	0.0060 (17)	−0.0061 (18)

Geometric parameters (Å, º) top

S1—C2	1.723 (3)	C25—C26	1.511 (8)
S1—C7A	1.745 (3)	C25—H25A	0.9700
C2—N2	1.338 (4)	C25—H25B	0.9700
C2—C3	1.403 (4)	C26—C27	1.524 (9)
C3—C37	1.433 (4)	C26—H26A	0.9700
C3—C3A	1.459 (4)	C26—H26B	0.9700
C3A—C7A	1.339 (3)	C27—H27A	0.9700
C3A—C4	1.511 (4)	C27—H27B	0.9700
C4—C5	1.531 (7)	N2—H2A	0.8600
C4—H4A	0.9700	N2—H2B	0.8600
C4—H4B	0.9700	C37—O37	1.244 (3)
C5—C6	1.513 (6)	C37—C31	1.498 (4)
C5—H5A	0.9700	C31—C36	1.379 (4)
C5—H5B	0.9700	C31—C32	1.386 (4)
C6—C7	1.524 (7)	C32—C33	1.379 (5)
C6—H6A	0.9700	C32—H32	0.9300
C6—H6B	0.9700	C33—C34	1.379 (6)
C7—C7A	1.502 (4)	C33—H33	0.9300
C7—H7A	0.9700	C34—C35	1.363 (5)
C7—H7B	0.9700	C34—H34	0.9300
C24—C25	1.531 (9)	C35—C36	1.370 (5)
C24—H24A	0.9700	C35—H35	0.9300
C24—H24B	0.9700	C36—H36	0.9300

C2—S1—C7A	91.63 (13)	C26—C25—C24	110.6 (11)
N2—C2—C3	127.5 (3)	C26—C25—H25A	109.5
N2—C2—S1	120.9 (2)	C24—C25—H25A	109.5
C3—C2—S1	111.7 (2)	C26—C25—H25B	109.5
C2—C3—C37	119.2 (3)	C24—C25—H25B	109.5
C2—C3—C3A	111.0 (2)	H25A—C25—H25B	108.1
C37—C3—C3A	129.8 (2)	C25—C26—C27	110.1 (11)
C7A—C3A—C3	113.0 (2)	C25—C26—H26A	109.7
C7A—C3A—C4	120.7 (3)	C27—C26—H26A	109.7
C3—C3A—C4	126.1 (2)	C25—C26—H26B	109.7
C3A—C4—C5	110.4 (4)	C27—C26—H26B	109.7
C3A—C4—H4A	109.6	H26A—C26—H26B	108.2
C5—C4—H4A	109.6	C26—C27—H27A	109.9
C3A—C4—H4B	109.6	C26—C27—H27B	109.9
C5—C4—H4B	109.6	H27A—C27—H27B	108.3
H4A—C4—H4B	108.1	C2—N2—H2A	120.0
C6—C5—C4	110.9 (6)	C2—N2—H2B	120.0
C6—C5—H5A	109.5	H2A—N2—H2B	120.0
C4—C5—H5A	109.5	O37—C37—C3	121.1 (3)
C6—C5—H5B	109.5	O37—C37—C31	117.5 (3)
C4—C5—H5B	109.5	C3—C37—C31	121.3 (3)
H5A—C5—H5B	108.1	C36—C31—C32	118.9 (3)
C5—C6—C7	109.8 (6)	C36—C31—C37	121.3 (3)
C5—C6—H6A	109.7	C32—C31—C37	119.6 (3)
C7—C6—H6A	109.7	C33—C32—C31	119.8 (4)
C5—C6—H6B	109.7	C33—C32—H32	120.1
C7—C6—H6B	109.7	C31—C32—H32	120.1
H6A—C6—H6B	108.2	C34—C33—C32	120.1 (4)
C7A—C7—C6	109.1 (4)	C34—C33—H33	119.9
C7A—C7—H7A	109.9	C32—C33—H33	119.9
C6—C7—H7A	109.9	C35—C34—C33	120.1 (4)
C7A—C7—H7B	109.9	C35—C34—H34	119.9
C6—C7—H7B	109.9	C33—C34—H34	119.9
H7A—C7—H7B	108.3	C34—C35—C36	119.9 (4)
C3A—C7A—C7	126.9 (3)	C34—C35—H35	120.0
C3A—C7A—S1	112.6 (2)	C36—C35—H35	120.0
C7—C7A—S1	120.2 (2)	C35—C36—C31	121.1 (3)
C25—C24—H24A	109.6	C35—C36—H36	119.5
C25—C24—H24B	109.6	C31—C36—H36	119.5
H24A—C24—H24B	108.1

C7A—S1—C2—N2	−177.3 (3)	C6—C7—C7A—S1	171.3 (5)
C7A—S1—C2—C3	2.7 (2)	C2—S1—C7A—C3A	−1.0 (3)
N2—C2—C3—C37	−3.4 (5)	C2—S1—C7A—C7	173.3 (6)
S1—C2—C3—C37	176.6 (2)	C24—C25—C26—C27	66.1 (18)
N2—C2—C3—C3A	176.4 (3)	C2—C3—C37—O37	17.5 (4)
S1—C2—C3—C3A	−3.7 (3)	C3A—C3—C37—O37	−162.2 (3)
C2—C3—C3A—C7A	3.0 (4)	C2—C3—C37—C31	−159.5 (3)
C37—C3—C3A—C7A	−177.3 (3)	C3A—C3—C37—C31	20.8 (5)
C2—C3—C3A—C4	−171.5 (6)	O37—C37—C31—C36	−130.1 (3)
C37—C3—C3A—C4	8.2 (8)	C3—C37—C31—C36	47.0 (5)
C7A—C3A—C4—C5	−16.5 (11)	O37—C37—C31—C32	45.3 (4)
C3—C3A—C4—C5	157.6 (5)	C3—C37—C31—C32	−137.6 (3)
C3A—C4—C5—C6	49.0 (11)	C36—C31—C32—C33	−1.5 (5)
C4—C5—C6—C7	−66.4 (11)	C37—C31—C32—C33	−177.0 (3)
C5—C6—C7—C7A	46.7 (11)	C31—C32—C33—C34	0.9 (6)
C3—C3A—C7A—C7	−174.7 (6)	C32—C33—C34—C35	0.8 (6)
C4—C3A—C7A—C7	0.1 (10)	C33—C34—C35—C36	−1.8 (7)
C3—C3A—C7A—S1	−0.9 (3)	C34—C35—C36—C31	1.2 (6)
C4—C3A—C7A—S1	173.9 (6)	C32—C31—C36—C35	0.5 (6)
C6—C7—C7A—C3A	−15.3 (11)	C37—C31—C36—C35	175.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O37	0.86	2.07	2.666 (3)	125
N2—H2B···O37ⁱ	0.86	2.03	2.831 (3)	156

Symmetry code: (i) x−1/2, −y+3/2, z.

Selected geometric parameters (Å, °) for compounds (I)–(VI) top

(a)	Ring-puckering parameters
		Q	θ	φ
(I), major		0.516 (5)	49.0 (6)	145.5 (8)
(I), minor		0.50 (2)	139 (2)	332 (4)
(II), major		0.514 (9)	48.3 (11)	150.4 (17)
(II), minor		0.538 (18)	134 (2)	330 (3)
(III), major		0.507 (5)	50.0 (6)	138.7 (8)
(III), minor		0.489 (19)	143 (2)	327 (4)
(IV), molecule 1		0.467 (3)	50.7 (4)	150.5 (5)
(IV), molecule 2		0.486 (4)	51.5 (4)	143.5 (5)
(V)		0.5098 (19)	53.3 (2)	142.2 (2)
(VI), major		0.517 (6)	49.7 (7)	148.9 (9)
(VI), minor		0.51 (3)	135 (3)	331 (6)

(b)	Torsion angles
	τ₁	τ₂	τ₃	τ₄
(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

Compound	D—H···A	D—H	H···A	D···A	D—H···A
(I)	N1—H1···O37	0.86	2.01	2.650 (3)	130
(II)	N1—H1···O37	0.86	1.99	2.641 (3)	132
	C3—H3···Cg1ⁱ	0.93	2.76	3.676 (4)	169
	C14—H14A···Cg1	0.97	2.96	3.475 (9)	114
	C24—H24A···Cg1	0.97	2.73	3.530 (17)	140
(III)	N1—H1···O37	0.86	2.08	2.718 (2)	130
	C3—H3···O37ⁱⁱ	0.93	2.50	3.326 (3)	148
	C17—H17A···O7ⁱⁱⁱ	0.97	2.59	3.494 (12)	156
	C4—H4···Cg1^iv	0.93	2.85	3.635 (2)	143
	C35—H35···Cg2^v	0.93	2.75	3.520 (2)	141
(IV)	N11—H11···O12	0.86	1.95	2.630 (3)	136
	N11—H11···O137	0.86	2.11	2.731 (3)	128
	N21—H21···O22	0.86	1.93	2.616 (3)	136
	N21—H21···O237	0.86	2.13	2.748 (3)	129
	C134—H134···O27	0.93	2.49	3.232 (4)	137
	C235—H235···Cg3^vi	0.93	2.95	3.869 (3)	170
(VI)	N2—H2A···O37	0.86	2.07	2.666 (3)	125
	N2—H2B···O37^vii	0.86	2.03	2.831 (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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