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In the structures of 2-(4-chloro­phenyl)-4-(2-hydroxyphenyl)-2,3-di­hydro-1,5-benzo­thia­zepine, C21H16ClNOS, 4-(2-hy­droxy­phenyl)-2-(4-tolyl)-2,3-di­hydro-1,5-ben­zo­thia­zepine, C22H19NOS, and 4-(2-hydroxyphenyl)-2-(3-methoxy­phenyl)-2,3-di­hydro-1,5-benzo­thia­zepine, C22H19NO2S, the central seven-membered heterocyclic rings adopt twist-boat conformations in which the N atoms are involved in strong intramolecular hydrogen bonds with the hydroxyl H atoms, resulting in six-membered rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103008345/fr1416sup1.cif
Contains datablocks Global, IVa, IVb, IVc

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103008345/fr1416IVasup2.hkl
Contains datablock IVa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103008345/fr1416IVbsup3.hkl
Contains datablock IVb

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103008345/fr1416IVcsup4.hkl
Contains datablock IVc

CCDC references: 214392; 214393; 214394

Comment top

Many chemotherapeutic applications have been associated with benzothiazepine derivatives, such as diltiazem, which is used as a calcium channel blocker (Chaffman & Brogden, 1985), an angiotensin-converting enzyme inhibitor (Itoh et al., 1986), and an anticonvulsant and tranquilizing agent (Bock et al., 1989). Calcium channel blockers are important cardiovascular drugs for the management of angina pectoris and hypertension and may have applications in additional therapeutic areas (Godfraind et al., 1986). The importance of the methoxyphenyl moiety in biologically active compounds belonging to the benzothiazepine series of drugs has also been reported (Pant et al., 1994). Following these studies and continuing our investigations in this area (Ansari et al., 2002), we have reacted 2-hydroxy acetophenone, (I), with substituted benzaldehyde, (II), (see Scheme; R = Cl, CH3 or H and R' = H, H, or OCH3, respectively). The reaction yielded chalcones, (III), which on treatment with o-aminothiophenol in equimolar quantities in acidified methanol led to the formation of 4-chlorophenyl, 4-toluyl and 3-methoxyphenyl derivatives of 4-(2'-hydroxylphenyl)-2-phenyl −2,3-dihydro-1,5-benzothiazepine, (IVa)–(IVc), respectively. In this paper, we report the crystal structures of (IVa)–(IVc).

The Figs. 1–3 show the structures of (IVa)–(IVc), respectively. In all three structures, the central seven-membered heterocyclic rings adopt twist- boat conformations, such that atoms C1, C5, C6 and N7 are essentially planar and the remaining atoms lie above this plane. The distances of the remaining atoms of the heterocyclic ring from the planes in (IVa)–(IVc) are, respectively, 0.997 (4), 0.983 (3) and 0.983 (3) Å for atom C2; 2.287 (3), 2.283 (2) and 2.268 (4) Å for atom S3; and 1.393 (4), 1.388 (3) and 1.375 (2) Å for atom C4. Atoms C1, C5, C6 and N7 of the heterocyclic rings are coplanar with the hydroxyphenyl rings in the three structures, with atoms C1 and O24 lying on the opposite sides of the mean planes passing through these atoms (plane 1), the maximum deviations for C1 being 0.181 (2), 0.1307 (12) and 0.1531 (11) Å and for O24 being 0.095 (2), 0.0591 (11) and 0.0590 (10) Å for (IVa)–(IVc), respectively. Moreover, the C12–C17 phenyl ring (plane 2) is almost coplanar with plane 1 in (IVa) [the angle between the mean planes? is 3.48 (12)°] and is inclined at 18.39 (7) and 65.88 (5)° in (IVb) and (IVc), respectively. The angles between the mean planes formed by the C1/C2/C8–C11 (plane 3) and C12–C17 (plane 4) phenyl rings are 51.3 (9), 63.68 (5) and 64.05 (6)°, respectively, while the C18—C23 phenyl ring (plane 5) is oriented with respect to plane 3 at 52.94 (9), 48.71 (6) and 52.49 (5)° in (IVa)–(IVc), respectively.

In all three structures, atom N7 of the heterocyclic ring is involved in intramolecular hydrogen bonds with the hydroxyl H atom, resulting in a six-membered ring; details of hydrogen-bonding geometry are provided in Tables 2, 4 and 6 for (IVa)-(IVc), respectively. Note that in (IVb), atom S3 is involved in short intramolecular contacts with a phenyl H atom [S3···H17 = 2.78 Å]. The corresponding contact in (IVa) is 2.91 Å, while (IVc) displays no such contact. Crystal-packing forces and the orientation of the phenyl rings are probably responsible for these observations.

The molecular dimensions in the three structures are unexceptional. A search of the November 2002 release of the Cambridge Structural Database (Allen, 2002) showed only five structures containing a heterocyclic seven- membered ring analogous to that in (IVa)–(IVc).

Experimental top

Syntheses of the chalcones, (III), were carried out according to the procedures described by Furniss et al. (1989). Aqueous solutions of NaOH (60.0 ml, 4.0 M) were added to rectified spirit (35.0 ml) in conical flasks fitted with mechanical stirrers. The flasks were cooled in an ice bath and freshly distilled o-hydroxy acetophenone, (I), (0.01 mol) was added to each. To these solutions were added, while stirring, substituted benzaldehydes, (II), (0.01 mol). The temperature was kept at about 298 K and the reaction mixtures were stirred vigorously for 2–3 h until the mixtures became thick. The reaction mixtures were kept at 273–277 K overnight. The solid masses thus obtained were neutralized with HCl, and the precipitates separated were crystallized from equeous ethanol. The benzothiazepine derivatives (IVa)–(IVc) were synthesized according to the procedure reported by Svetlik et al. (1989). To the corresponding solutions of chalcones, (III), (0.02 mol) in dry methanol (100–150 ml), which were acidified by adding conconcentrated HCl (five drops), was added o-amino thiophenol (0.02 mol). The mixtures were refluxed until crystalline solids separated out. After cooling, solid benzothiazepine derivatives were collected, washed with ether and cold methanol, and recrystallized from aqueous ethanol.

Refinement top

For the three structures, the H atoms were located from difference Fourier syntheses and were included in the refinements at idealized positions, with C—H distances of 0.95–1.00 and an O—H distance of 0.84 Å and with isotropic thermal displacement parameters of 1.5 (hydroxyl H atoms) or 1.2 (the remaining H atoms) times the equivalent thermal displacement parameters of the parent atoms. The methyl H atoms in (IVb) were disordered over six sites and were included in the refinement using the DFIX 123 command in SHELXL97. The final difference maps were free of any chemically significant features.

Computing details top

For all compounds, data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997). Data reduction: HKL SCALEPACK (Otwinowski & Minor, 1997) for (IVa); SCALEPACK (Otwinowski & Minor, 1997) for (IVb), (IVc). For all compounds, program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of (IVa), with displacement ellipsoids plotted at the 50% probability level.
[Figure 2] Fig. 2. ORTEPII (Johnson, 1976) drawing of (IVb), with displacement ellipsoids plotted at the 50% probability level; only three of the disordered methyl H atoms are shown.
[Figure 3] Fig. 3. ORTEPII (Johnson, 1976) drawing of (IVc), with displacement ellipsoids plotted at the 50% probability level.
(IVa) 2-(4-chlorophenyl)-4-(2-hydroxylphenyl)-2-phenyl-2,3-dihydro-1,5- benzothiazepine top
Crystal data top
C21H16ClNOSF(000) = 760
Mr = 365.86Dx = 1.419 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9054 reflections
a = 18.036 (9) Åθ = 4.1–25.0°
b = 4.836 (2) ŵ = 0.35 mm1
c = 19.790 (11) ÅT = 173 K
β = 97.02 (2)°Needle, yellow
V = 1713.2 (15) Å30.15 × 0.08 × 0.06 mm
Z = 4
Data collection top
Nonius KappaCCD Area Detector
diffractometer
2987 independent reflections
Radiation source: fine-focus sealed tube2093 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ω and ϕ scansθmax = 25.0°, θmin = 4.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 2120
Tmin = 0.901, Tmax = 0.982k = 55
9054 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.058P)2]
where P = (Fo2 + 2Fc2)/3
2987 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C21H16ClNOSV = 1713.2 (15) Å3
Mr = 365.86Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.036 (9) ŵ = 0.35 mm1
b = 4.836 (2) ÅT = 173 K
c = 19.790 (11) Å0.15 × 0.08 × 0.06 mm
β = 97.02 (2)°
Data collection top
Nonius KappaCCD Area Detector
diffractometer
2987 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
2093 reflections with I > 2σ(I)
Tmin = 0.901, Tmax = 0.982Rint = 0.064
9054 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
2987 reflectionsΔρmin = 0.32 e Å3
227 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.89138 (13)0.3863 (5)0.59156 (12)0.0292 (6)
C20.85176 (13)0.3364 (5)0.64726 (13)0.0289 (6)
S30.78231 (3)0.07528 (13)0.64579 (3)0.0319 (2)
C40.70901 (13)0.1897 (5)0.57907 (13)0.0293 (6)
H40.68780.01890.55570.035*
C50.74426 (13)0.3586 (5)0.52527 (13)0.0307 (6)
H5A0.70580.39700.48630.037*
H5B0.76200.53790.54520.037*
C60.80873 (13)0.2076 (5)0.50029 (13)0.0293 (6)
N70.87641 (11)0.2375 (4)0.52969 (10)0.0307 (5)
C80.95000 (14)0.5748 (5)0.59769 (13)0.0333 (6)
H80.97720.60670.56020.040*
C90.96897 (14)0.7162 (5)0.65808 (14)0.0345 (6)
H91.00790.84940.66140.041*
C100.93128 (14)0.6641 (5)0.71396 (14)0.0346 (6)
H100.94530.75830.75570.041*
C110.87314 (14)0.4741 (5)0.70867 (13)0.0324 (6)
H110.84770.43740.74700.039*
C120.64449 (13)0.3399 (5)0.60472 (13)0.0302 (6)
C130.57203 (14)0.2881 (6)0.57518 (14)0.0405 (7)
H130.56380.15590.53960.049*
C140.51160 (15)0.4246 (6)0.59638 (15)0.0442 (7)
H140.46230.38700.57560.053*
C150.52385 (14)0.6161 (6)0.64814 (14)0.0371 (7)
C160.59512 (14)0.6760 (5)0.67793 (14)0.0364 (6)
H160.60310.81140.71280.044*
C170.65493 (13)0.5363 (5)0.65639 (13)0.0326 (6)
H170.70410.57530.67730.039*
C180.79630 (14)0.0132 (5)0.44247 (12)0.0296 (6)
C190.72434 (14)0.0415 (6)0.41025 (13)0.0369 (6)
H190.68330.05670.42440.044*
C200.71120 (16)0.2336 (6)0.35868 (13)0.0417 (7)
H200.66190.26600.33740.050*
C210.77109 (17)0.3793 (6)0.33824 (14)0.0425 (7)
H210.76250.51340.30310.051*
C220.84269 (16)0.3304 (6)0.36864 (14)0.0406 (7)
H220.88320.43080.35420.049*
C230.85631 (14)0.1354 (5)0.42036 (13)0.0325 (6)
O240.92787 (9)0.0941 (4)0.44721 (9)0.0414 (5)
H240.92910.01310.48070.062*
Cl250.44800 (4)0.78184 (17)0.67724 (4)0.0541 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0245 (13)0.0320 (14)0.0307 (14)0.0054 (11)0.0023 (10)0.0001 (11)
C20.0229 (13)0.0306 (14)0.0324 (14)0.0038 (10)0.0002 (11)0.0041 (11)
S30.0287 (4)0.0313 (4)0.0349 (4)0.0005 (3)0.0007 (3)0.0059 (3)
C40.0288 (13)0.0289 (14)0.0295 (14)0.0014 (11)0.0005 (11)0.0023 (11)
C50.0300 (13)0.0316 (14)0.0297 (14)0.0035 (11)0.0007 (11)0.0014 (11)
C60.0288 (13)0.0291 (14)0.0299 (14)0.0034 (11)0.0036 (11)0.0049 (11)
N70.0287 (11)0.0334 (12)0.0303 (12)0.0017 (9)0.0043 (9)0.0003 (10)
C80.0284 (13)0.0352 (15)0.0361 (15)0.0010 (12)0.0034 (11)0.0042 (12)
C90.0271 (13)0.0341 (15)0.0414 (16)0.0015 (11)0.0005 (12)0.0021 (13)
C100.0325 (14)0.0328 (15)0.0364 (16)0.0048 (12)0.0036 (12)0.0007 (12)
C110.0323 (14)0.0327 (15)0.0315 (15)0.0063 (12)0.0014 (11)0.0043 (12)
C120.0290 (13)0.0303 (14)0.0311 (15)0.0010 (11)0.0023 (11)0.0049 (11)
C130.0308 (15)0.0483 (17)0.0406 (17)0.0020 (13)0.0028 (12)0.0065 (13)
C140.0260 (14)0.0544 (19)0.0504 (18)0.0010 (13)0.0024 (12)0.0062 (15)
C150.0282 (14)0.0394 (16)0.0449 (17)0.0061 (12)0.0091 (12)0.0039 (13)
C160.0375 (15)0.0354 (15)0.0370 (16)0.0015 (12)0.0072 (12)0.0016 (12)
C170.0227 (13)0.0344 (15)0.0407 (16)0.0021 (11)0.0033 (11)0.0006 (12)
C180.0322 (14)0.0304 (14)0.0264 (14)0.0002 (11)0.0049 (11)0.0025 (11)
C190.0358 (15)0.0433 (16)0.0315 (15)0.0032 (12)0.0040 (12)0.0002 (13)
C200.0435 (16)0.0443 (17)0.0352 (16)0.0016 (13)0.0039 (13)0.0034 (14)
C210.0585 (19)0.0412 (17)0.0277 (15)0.0022 (14)0.0052 (13)0.0048 (13)
C220.0485 (17)0.0408 (16)0.0348 (16)0.0026 (13)0.0138 (13)0.0025 (13)
C230.0349 (15)0.0362 (15)0.0274 (14)0.0007 (12)0.0077 (11)0.0064 (11)
O240.0331 (10)0.0493 (12)0.0432 (12)0.0031 (9)0.0100 (8)0.0089 (9)
Cl250.0342 (4)0.0629 (5)0.0673 (6)0.0121 (3)0.0146 (4)0.0054 (4)
Geometric parameters (Å, º) top
C1—C81.390 (3)C12—C171.391 (4)
C1—C21.406 (4)C13—C141.382 (4)
C1—N71.418 (3)C13—H130.9500
C2—C111.398 (3)C14—C151.378 (4)
C2—S31.776 (3)C14—H140.9500
S3—C41.836 (2)C15—C161.378 (4)
C4—C121.511 (4)C15—Cl251.743 (3)
C4—C51.540 (4)C16—C171.383 (4)
C4—H41.0000C16—H160.9500
C5—C61.507 (3)C17—H170.9500
C5—H5A0.9900C18—C191.400 (3)
C5—H5B0.9900C18—C231.413 (4)
C6—N71.295 (3)C19—C201.379 (4)
C6—C181.477 (3)C19—H190.9500
C8—C91.383 (4)C20—C211.390 (4)
C8—H80.9500C20—H200.9500
C9—C101.390 (4)C21—C221.377 (4)
C9—H90.9500C21—H210.9500
C10—C111.389 (4)C22—C231.391 (4)
C10—H100.9500C22—H220.9500
C11—H110.9500C23—O241.349 (3)
C12—C131.388 (3)O24—H240.8400
C8—C1—C2119.9 (2)C13—C12—C4119.7 (2)
C8—C1—N7118.1 (2)C17—C12—C4122.3 (2)
C2—C1—N7121.9 (2)C14—C13—C12121.5 (3)
C11—C2—C1119.1 (2)C14—C13—H13119.2
C11—C2—S3118.15 (19)C12—C13—H13119.2
C1—C2—S3122.30 (19)C15—C14—C13119.0 (2)
C2—S3—C4103.99 (12)C15—C14—H14120.5
C12—C4—C5112.2 (2)C13—C14—H14120.5
C12—C4—S3114.81 (18)C16—C15—C14121.0 (2)
C5—C4—S3109.59 (17)C16—C15—Cl25119.4 (2)
C12—C4—H4106.6C14—C15—Cl25119.6 (2)
C5—C4—H4106.6C15—C16—C17119.2 (3)
S3—C4—H4106.6C15—C16—H16120.4
C6—C5—C4111.7 (2)C17—C16—H16120.4
C6—C5—H5A109.3C16—C17—C12121.3 (2)
C4—C5—H5A109.3C16—C17—H17119.4
C6—C5—H5B109.3C12—C17—H17119.4
C4—C5—H5B109.3C19—C18—C23117.8 (2)
H5A—C5—H5B107.9C19—C18—C6121.2 (2)
N7—C6—C18117.7 (2)C23—C18—C6121.0 (2)
N7—C6—C5121.4 (2)C20—C19—C18122.0 (2)
C18—C6—C5120.8 (2)C20—C19—H19119.0
C6—N7—C1121.0 (2)C18—C19—H19119.0
C9—C8—C1120.3 (2)C19—C20—C21119.2 (2)
C9—C8—H8119.8C19—C20—H20120.4
C1—C8—H8119.8C21—C20—H20120.4
C8—C9—C10120.3 (2)C22—C21—C20120.4 (2)
C8—C9—H9119.9C22—C21—H21119.8
C10—C9—H9119.9C20—C21—H21119.8
C11—C10—C9119.9 (2)C21—C22—C23120.6 (3)
C11—C10—H10120.1C21—C22—H22119.7
C9—C10—H10120.1C23—C22—H22119.7
C10—C11—C2120.4 (2)O24—C23—C22117.7 (2)
C10—C11—H11119.8O24—C23—C18122.3 (2)
C2—C11—H11119.8C22—C23—C18120.0 (2)
C13—C12—C17117.9 (2)C23—O24—H24109.5
C8—C1—C2—C111.3 (3)S3—C4—C12—C1742.2 (3)
N7—C1—C2—C11174.9 (2)C17—C12—C13—C140.5 (4)
C8—C1—C2—S3173.85 (19)C4—C12—C13—C14178.9 (3)
N7—C1—C2—S32.3 (3)C12—C13—C14—C150.1 (4)
C11—C2—S3—C4122.96 (19)C13—C14—C15—C161.1 (4)
C1—C2—S3—C464.4 (2)C13—C14—C15—Cl25178.0 (2)
C2—S3—C4—C1297.9 (2)C14—C15—C16—C171.5 (4)
C2—S3—C4—C529.3 (2)Cl25—C15—C16—C17177.6 (2)
C12—C4—C5—C6179.7 (2)C15—C16—C17—C120.9 (4)
S3—C4—C5—C651.0 (2)C13—C12—C17—C160.1 (4)
C4—C5—C6—N790.1 (3)C4—C12—C17—C16178.5 (2)
C4—C5—C6—C1888.0 (3)N7—C6—C18—C19176.6 (2)
C18—C6—N7—C1170.2 (2)C5—C6—C18—C191.5 (4)
C5—C6—N7—C17.9 (3)N7—C6—C18—C230.2 (4)
C8—C1—N7—C6135.1 (2)C5—C6—C18—C23177.9 (2)
C2—C1—N7—C648.7 (3)C23—C18—C19—C200.1 (4)
C2—C1—C8—C90.8 (4)C6—C18—C19—C20176.4 (2)
N7—C1—C8—C9177.1 (2)C18—C19—C20—C210.5 (4)
C1—C8—C9—C102.2 (4)C19—C20—C21—C220.6 (4)
C8—C9—C10—C111.5 (4)C20—C21—C22—C230.2 (4)
C9—C10—C11—C20.6 (4)C21—C22—C23—O24178.9 (2)
C1—C2—C11—C102.0 (3)C21—C22—C23—C180.4 (4)
S3—C2—C11—C10174.86 (18)C19—C18—C23—O24178.7 (2)
C5—C4—C12—C1394.6 (3)C6—C18—C23—O244.8 (4)
S3—C4—C12—C13139.4 (2)C19—C18—C23—C220.6 (4)
C5—C4—C12—C1783.7 (3)C6—C18—C23—C22175.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O24—H24···N70.841.802.543 (3)146
(IVb) 4-(2-hydroxylphenyl)-2-phenyl-2-(4-tolyl)-2,3-dihydro-1,5-benzothiazepine top
Crystal data top
C22H19NOSF(000) = 728
Mr = 345.44Dx = 1.335 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8207 reflections
a = 4.8678 (11) Åθ = 3.6–30.0°
b = 17.563 (3) ŵ = 0.20 mm1
c = 20.129 (5) ÅT = 173 K
β = 93.078 (8)°Needle, yellow
V = 1718.4 (6) Å30.22 × 0.12 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD Area Detector
diffractometer
4972 independent reflections
Radiation source: fine-focus sealed tube3195 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.037
ω and ϕ scansθmax = 30.0°, θmin = 3.6°
Absorption correction: multi-scan
SORTAV: (Blessing, 1997)
h = 66
Tmin = 0.906, Tmax = 0.988k = 2124
8207 measured reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0547P)2 + 0.2349P]
where P = (Fo2 + 2Fc2)/3
4972 reflections(Δ/σ)max = 0.001
228 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C22H19NOSV = 1718.4 (6) Å3
Mr = 345.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.8678 (11) ŵ = 0.20 mm1
b = 17.563 (3) ÅT = 173 K
c = 20.129 (5) Å0.22 × 0.12 × 0.08 mm
β = 93.078 (8)°
Data collection top
Nonius KappaCCD Area Detector
diffractometer
4972 independent reflections
Absorption correction: multi-scan
SORTAV: (Blessing, 1997)
3195 reflections with I > 2.0σ(I)
Tmin = 0.906, Tmax = 0.988Rint = 0.037
8207 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 0.99Δρmax = 0.23 e Å3
4972 reflectionsΔρmin = 0.32 e Å3
228 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S30.75407 (8)0.97332 (2)0.76225 (2)0.02867 (12)
O240.4199 (2)1.08023 (7)0.53490 (6)0.0372 (3)
H240.53551.04840.55020.056*
N70.7929 (3)1.02570 (7)0.61496 (7)0.0286 (3)
C10.9544 (3)0.96218 (8)0.63529 (8)0.0275 (4)
C20.9610 (3)0.93421 (8)0.70116 (8)0.0261 (3)
C40.8922 (3)1.07002 (8)0.77382 (8)0.0248 (3)
H40.73341.10380.78300.030*
C51.0070 (3)1.09768 (8)0.70857 (7)0.0241 (3)
H5A1.05681.15220.71300.029*
H5B1.17661.06890.70030.029*
C60.8036 (3)1.08796 (8)0.64949 (8)0.0255 (3)
C81.1034 (4)0.92505 (9)0.58796 (9)0.0337 (4)
H81.09460.94290.54330.040*
C91.2640 (4)0.86245 (10)0.60509 (9)0.0372 (4)
H91.36930.83860.57260.045*
C101.2719 (4)0.83440 (9)0.66957 (9)0.0357 (4)
H101.38130.79110.68120.043*
C111.1193 (3)0.86986 (8)0.71693 (8)0.0300 (4)
H111.12270.85000.76090.036*
C121.1067 (3)1.08076 (9)0.83093 (8)0.0261 (3)
C131.1624 (4)1.15475 (10)0.85255 (9)0.0356 (4)
H131.06211.19590.83250.043*
C141.3616 (4)1.16946 (10)0.90279 (9)0.0415 (4)
H141.39291.22040.91720.050*
C151.5161 (3)1.11078 (11)0.93230 (8)0.0385 (4)
C161.4609 (4)1.03739 (11)0.91070 (9)0.0381 (4)
H161.56360.99630.93020.046*
C171.2574 (3)1.02219 (9)0.86084 (8)0.0310 (4)
H171.22230.97110.84740.037*
C180.6112 (3)1.14960 (8)0.63026 (8)0.0254 (3)
C190.5986 (3)1.21651 (9)0.66801 (8)0.0302 (4)
H190.72061.22240.70610.036*
C200.4140 (4)1.27421 (9)0.65152 (9)0.0353 (4)
H200.40871.31880.67810.042*
C210.2370 (4)1.26611 (10)0.59573 (9)0.0388 (4)
H210.11031.30560.58380.047*
C220.2431 (3)1.20111 (10)0.55730 (9)0.0372 (4)
H220.12101.19640.51910.045*
C230.4259 (3)1.14234 (9)0.57384 (8)0.0287 (4)
C251.7345 (4)1.12760 (13)0.98684 (9)0.0541 (6)
H25A1.74261.18260.99500.081*0.50
H25B1.91361.10980.97310.081*0.50
H25C1.68861.10131.02770.081*0.50
H25D1.82061.07991.00220.081*0.50
H25E1.64961.15261.02410.081*0.50
H25F1.87461.16120.96950.081*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S30.0290 (2)0.0248 (2)0.0324 (2)0.00593 (16)0.00292 (16)0.00182 (16)
O240.0432 (7)0.0354 (6)0.0317 (7)0.0064 (5)0.0106 (5)0.0039 (5)
N70.0311 (7)0.0258 (7)0.0284 (7)0.0027 (6)0.0029 (6)0.0014 (6)
C10.0287 (8)0.0236 (7)0.0294 (9)0.0008 (6)0.0048 (7)0.0024 (6)
C20.0264 (8)0.0220 (7)0.0297 (9)0.0034 (6)0.0015 (6)0.0023 (6)
C40.0251 (7)0.0210 (7)0.0280 (8)0.0018 (6)0.0020 (6)0.0012 (6)
C50.0241 (7)0.0217 (7)0.0262 (8)0.0009 (6)0.0017 (6)0.0003 (6)
C60.0257 (8)0.0245 (8)0.0259 (8)0.0016 (6)0.0014 (6)0.0022 (6)
C80.0435 (10)0.0282 (8)0.0292 (9)0.0038 (7)0.0009 (8)0.0013 (7)
C90.0450 (10)0.0292 (8)0.0378 (10)0.0075 (8)0.0051 (8)0.0043 (7)
C100.0385 (9)0.0250 (8)0.0432 (11)0.0051 (7)0.0020 (8)0.0021 (7)
C110.0358 (9)0.0226 (8)0.0312 (9)0.0028 (7)0.0022 (7)0.0015 (7)
C120.0254 (8)0.0299 (8)0.0230 (8)0.0032 (6)0.0012 (6)0.0005 (6)
C130.0432 (10)0.0294 (9)0.0337 (10)0.0062 (7)0.0038 (8)0.0012 (7)
C140.0486 (11)0.0421 (10)0.0332 (10)0.0178 (9)0.0024 (8)0.0053 (8)
C150.0321 (9)0.0597 (12)0.0235 (9)0.0124 (8)0.0001 (7)0.0014 (8)
C160.0328 (9)0.0521 (11)0.0290 (9)0.0025 (8)0.0030 (7)0.0032 (8)
C170.0308 (8)0.0334 (9)0.0287 (9)0.0007 (7)0.0003 (7)0.0007 (7)
C180.0252 (8)0.0251 (7)0.0258 (8)0.0006 (6)0.0009 (6)0.0028 (6)
C190.0314 (9)0.0261 (8)0.0325 (9)0.0004 (7)0.0036 (7)0.0006 (7)
C200.0375 (9)0.0270 (8)0.0413 (10)0.0036 (7)0.0002 (8)0.0027 (7)
C210.0342 (9)0.0345 (9)0.0470 (11)0.0091 (7)0.0031 (8)0.0059 (8)
C220.0352 (9)0.0393 (10)0.0361 (10)0.0041 (8)0.0090 (8)0.0069 (8)
C230.0300 (8)0.0303 (8)0.0257 (9)0.0011 (7)0.0004 (7)0.0022 (7)
C250.0434 (11)0.0857 (16)0.0322 (11)0.0225 (11)0.0087 (9)0.0034 (10)
Geometric parameters (Å, º) top
S3—C21.7696 (17)C13—C141.387 (2)
S3—C41.8368 (15)C13—H130.9500
O24—C231.3427 (19)C14—C151.390 (3)
O24—H240.8400C14—H140.9500
N7—C61.2952 (19)C15—C161.382 (3)
N7—C11.4128 (19)C15—C251.516 (2)
C1—C81.390 (2)C16—C171.397 (2)
C1—C21.413 (2)C16—H160.9500
C2—C111.395 (2)C17—H170.9500
C4—C121.523 (2)C18—C191.403 (2)
C4—C51.534 (2)C18—C231.418 (2)
C4—H41.0000C19—C201.383 (2)
C5—C61.516 (2)C19—H190.9500
C5—H5A0.9900C20—C211.386 (2)
C5—H5B0.9900C20—H200.9500
C6—C181.470 (2)C21—C221.380 (2)
C8—C91.382 (2)C21—H210.9500
C8—H80.9500C22—C231.392 (2)
C9—C101.387 (2)C22—H220.9500
C9—H90.9500C25—H25A0.9800
C10—C111.387 (2)C25—H25B0.9800
C10—H100.9500C25—H25C0.9800
C11—H110.9500C25—H25D0.9800
C12—C171.383 (2)C25—H25E0.9800
C12—C131.392 (2)C25—H25F0.9800
C2—S3—C4103.23 (7)C14—C15—C25120.50 (18)
C23—O24—H24109.5C15—C16—C17121.49 (17)
C6—N7—C1120.37 (13)C15—C16—H16119.3
C8—C1—C2119.59 (14)C17—C16—H16119.3
C8—C1—N7118.32 (14)C12—C17—C16120.65 (15)
C2—C1—N7122.05 (14)C12—C17—H17119.7
C11—C2—C1118.67 (15)C16—C17—H17119.7
C11—C2—S3118.97 (13)C19—C18—C23117.71 (14)
C1—C2—S3122.16 (12)C19—C18—C6121.35 (14)
C12—C4—C5109.91 (12)C23—C18—C6120.92 (14)
C12—C4—S3116.21 (10)C20—C19—C18122.05 (15)
C5—C4—S3109.39 (10)C20—C19—H19119.0
C12—C4—H4107.0C18—C19—H19119.0
C5—C4—H4107.0C19—C20—C21119.15 (16)
S3—C4—H4107.0C19—C20—H20120.4
C6—C5—C4112.55 (12)C21—C20—H20120.4
C6—C5—H5A109.1C22—C21—C20120.52 (16)
C4—C5—H5A109.1C22—C21—H21119.7
C6—C5—H5B109.1C20—C21—H21119.7
C4—C5—H5B109.1C21—C22—C23120.81 (15)
H5A—C5—H5B107.8C21—C22—H22119.6
N7—C6—C18118.29 (13)C23—C22—H22119.6
N7—C6—C5121.45 (13)O24—C23—C22117.99 (14)
C18—C6—C5120.26 (13)O24—C23—C18122.26 (14)
C9—C8—C1120.73 (16)C22—C23—C18119.75 (15)
C9—C8—H8119.6C15—C25—H25A109.5
C1—C8—H8119.6C15—C25—H25B109.5
C8—C9—C10120.20 (17)H25A—C25—H25B109.5
C8—C9—H9119.9C15—C25—H25C109.5
C10—C9—H9119.9H25A—C25—H25C109.5
C11—C10—C9119.65 (15)H25B—C25—H25C109.5
C11—C10—H10120.2C15—C25—H25D109.5
C9—C10—H10120.2H25A—C25—H25D141.1
C10—C11—C2121.13 (15)H25B—C25—H25D56.3
C10—C11—H11119.4H25C—C25—H25D56.3
C2—C11—H11119.4C15—C25—H25E109.5
C17—C12—C13117.94 (14)H25A—C25—H25E56.3
C17—C12—C4124.27 (14)H25B—C25—H25E141.1
C13—C12—C4117.75 (13)H25C—C25—H25E56.3
C14—C13—C12121.21 (16)H25D—C25—H25E109.5
C14—C13—H13119.4C15—C25—H25F109.5
C12—C13—H13119.4H25A—C25—H25F56.3
C13—C14—C15120.97 (16)H25B—C25—H25F56.3
C13—C14—H14119.5H25C—C25—H25F141.1
C15—C14—H14119.5H25D—C25—H25F109.5
C16—C15—C14117.73 (15)H25E—C25—H25F109.5
C16—C15—C25121.77 (18)
C6—N7—C1—C8132.86 (17)S3—C4—C12—C13163.34 (13)
C6—N7—C1—C249.3 (2)C17—C12—C13—C140.3 (3)
C8—C1—C2—C110.3 (2)C4—C12—C13—C14177.81 (16)
N7—C1—C2—C11178.15 (13)C12—C13—C14—C151.3 (3)
C8—C1—C2—S3174.43 (12)C13—C14—C15—C161.1 (3)
N7—C1—C2—S33.4 (2)C13—C14—C15—C25179.60 (18)
C4—S3—C2—C11119.20 (12)C14—C15—C16—C170.1 (3)
C4—S3—C2—C166.04 (13)C25—C15—C16—C17179.36 (17)
C2—S3—C4—C1295.17 (13)C13—C12—C17—C160.7 (3)
C2—S3—C4—C529.98 (11)C4—C12—C17—C16176.61 (16)
C12—C4—C5—C6179.56 (12)C15—C16—C17—C120.8 (3)
S3—C4—C5—C650.84 (14)N7—C6—C18—C19175.68 (15)
C1—N7—C6—C18173.78 (14)C5—C6—C18—C194.0 (2)
C1—N7—C6—C55.9 (2)N7—C6—C18—C232.4 (2)
C4—C5—C6—N789.00 (18)C5—C6—C18—C23177.92 (14)
C4—C5—C6—C1890.67 (17)C23—C18—C19—C200.2 (3)
C2—C1—C8—C91.9 (2)C6—C18—C19—C20178.36 (16)
N7—C1—C8—C9179.79 (15)C18—C19—C20—C210.4 (3)
C1—C8—C9—C102.0 (3)C19—C20—C21—C220.4 (3)
C8—C9—C10—C110.5 (3)C20—C21—C22—C230.3 (3)
C9—C10—C11—C21.1 (2)C21—C22—C23—O24179.30 (17)
C1—C2—C11—C101.1 (2)C21—C22—C23—C180.9 (3)
S3—C2—C11—C10176.09 (12)C19—C18—C23—O24179.35 (15)
C5—C4—C12—C17105.51 (17)C6—C18—C23—O241.2 (2)
S3—C4—C12—C1719.4 (2)C19—C18—C23—C220.9 (2)
C5—C4—C12—C1371.78 (18)C6—C18—C23—C22179.05 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O24—H24···N70.841.802.5489 (17)147
(IVc) 4-(2-hydroxylphenyl)-2-(4-methoxyphenyl)-2-phenyl-2,3-dihydro-1,5- benzothiazepine top
Crystal data top
C22H19NO2SF(000) = 760
Mr = 361.44Dx = 1.340 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7583 reflections
a = 11.973 (2) Åθ = 3.7–27.5°
b = 16.224 (4) ŵ = 0.20 mm1
c = 9.250 (3) ÅT = 173 K
β = 94.437 (9)°Needle, yellow
V = 1791.4 (8) Å30.35 × 0.08 × 0.07 mm
Z = 4
Data collection top
Nonius KappaCCD Area Detector
diffractometer
4081 independent reflections
Radiation source: fine-focus sealed tube3007 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.031
ω and ϕ scansθmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan
SORTAV: (Blessing, 1997)
h = 1515
Tmin = 0.908, Tmax = 0.990k = 2121
7583 measured reflectionsl = 1112
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.05P)2 + 0.404P]
where P = (Fo2 + 2Fc2)/3
4081 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C22H19NO2SV = 1791.4 (8) Å3
Mr = 361.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.973 (2) ŵ = 0.20 mm1
b = 16.224 (4) ÅT = 173 K
c = 9.250 (3) Å0.35 × 0.08 × 0.07 mm
β = 94.437 (9)°
Data collection top
Nonius KappaCCD Area Detector
diffractometer
4081 independent reflections
Absorption correction: multi-scan
SORTAV: (Blessing, 1997)
3007 reflections with I > 2.0σ(I)
Tmin = 0.908, Tmax = 0.990Rint = 0.031
7583 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.02Δρmax = 0.23 e Å3
4081 reflectionsΔρmin = 0.36 e Å3
237 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.69018 (13)0.08409 (10)0.37331 (16)0.0276 (3)
C20.80306 (13)0.05878 (10)0.39202 (16)0.0298 (4)
S30.91453 (3)0.12995 (3)0.42612 (4)0.03332 (14)
C40.91081 (12)0.19439 (10)0.26106 (15)0.0258 (3)
H40.93150.25170.29290.031*
C50.79075 (12)0.19788 (10)0.19215 (15)0.0254 (3)
H5A0.78690.23790.11110.031*
H5B0.76990.14310.15150.031*
C60.70767 (12)0.22256 (10)0.29877 (15)0.0249 (3)
N70.65848 (10)0.16807 (8)0.37436 (13)0.0270 (3)
C80.60551 (15)0.02496 (11)0.36624 (17)0.0356 (4)
H80.52940.04180.35350.043*
C90.63128 (18)0.05791 (12)0.37763 (19)0.0454 (5)
H90.57300.09780.37120.054*
C100.74195 (18)0.08290 (12)0.39839 (19)0.0450 (5)
H100.75950.13980.40820.054*
C110.82705 (16)0.02487 (11)0.40485 (17)0.0379 (4)
H110.90280.04250.41820.046*
C120.99582 (13)0.16724 (9)0.15730 (16)0.0256 (3)
C130.96555 (13)0.12219 (10)0.03311 (17)0.0315 (4)
H130.88970.10620.01190.038*
C141.04633 (14)0.10037 (11)0.06055 (17)0.0353 (4)
H141.02500.06980.14590.042*
C151.15660 (14)0.12261 (11)0.03077 (18)0.0336 (4)
H151.21110.10780.09560.040*
C161.18799 (13)0.16686 (10)0.09443 (17)0.0304 (4)
C171.10791 (13)0.18948 (10)0.18856 (17)0.0285 (3)
H171.12940.22000.27390.034*
C180.68103 (12)0.30969 (10)0.32035 (15)0.0259 (3)
C190.73321 (14)0.37229 (10)0.24504 (17)0.0317 (4)
H190.78190.35740.17300.038*
C200.71591 (14)0.45478 (11)0.27241 (18)0.0360 (4)
H200.75210.49590.21990.043*
C210.64493 (15)0.47677 (11)0.37760 (19)0.0382 (4)
H210.63350.53340.39830.046*
C220.59088 (14)0.41730 (11)0.45220 (18)0.0356 (4)
H220.54200.43330.52330.043*
C230.60698 (13)0.33411 (10)0.42478 (16)0.0290 (4)
O240.55363 (10)0.27899 (8)0.50447 (12)0.0354 (3)
H240.57180.23100.48150.053*
O251.29948 (9)0.18624 (8)0.11383 (13)0.0420 (3)
C261.34418 (15)0.21132 (12)0.2539 (2)0.0410 (4)
H26A1.42570.21710.25410.049*
H26B1.32640.16980.32550.049*
H26C1.31130.26430.27850.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0303 (8)0.0327 (9)0.0200 (7)0.0024 (7)0.0025 (6)0.0013 (6)
C20.0323 (9)0.0374 (9)0.0198 (7)0.0056 (7)0.0039 (6)0.0015 (6)
S30.0248 (2)0.0517 (3)0.0231 (2)0.00411 (18)0.00084 (15)0.00421 (17)
C40.0238 (8)0.0320 (8)0.0218 (7)0.0020 (6)0.0027 (6)0.0022 (6)
C50.0247 (8)0.0316 (8)0.0200 (7)0.0040 (6)0.0021 (6)0.0010 (6)
C60.0214 (7)0.0337 (9)0.0192 (7)0.0026 (6)0.0016 (5)0.0001 (6)
N70.0227 (7)0.0332 (7)0.0248 (6)0.0028 (5)0.0015 (5)0.0008 (6)
C80.0365 (10)0.0405 (10)0.0299 (9)0.0035 (8)0.0021 (7)0.0006 (7)
C90.0627 (13)0.0383 (11)0.0352 (10)0.0119 (9)0.0040 (8)0.0031 (8)
C100.0713 (14)0.0326 (10)0.0317 (9)0.0079 (9)0.0081 (9)0.0006 (8)
C110.0459 (11)0.0417 (10)0.0267 (8)0.0149 (8)0.0061 (7)0.0014 (7)
C120.0254 (8)0.0268 (8)0.0250 (8)0.0033 (6)0.0044 (6)0.0003 (6)
C130.0268 (8)0.0390 (10)0.0288 (8)0.0006 (7)0.0029 (6)0.0066 (7)
C140.0376 (10)0.0414 (10)0.0271 (8)0.0045 (8)0.0038 (7)0.0075 (7)
C150.0341 (9)0.0390 (10)0.0291 (8)0.0062 (7)0.0119 (7)0.0006 (7)
C160.0255 (8)0.0336 (9)0.0327 (9)0.0001 (7)0.0074 (6)0.0029 (7)
C170.0280 (8)0.0312 (9)0.0266 (8)0.0006 (7)0.0040 (6)0.0033 (7)
C180.0224 (8)0.0331 (9)0.0217 (7)0.0067 (6)0.0010 (6)0.0011 (6)
C190.0334 (9)0.0354 (9)0.0264 (8)0.0038 (7)0.0034 (6)0.0010 (7)
C200.0373 (9)0.0331 (9)0.0377 (9)0.0028 (7)0.0036 (7)0.0041 (7)
C210.0390 (10)0.0326 (9)0.0422 (10)0.0099 (8)0.0015 (8)0.0027 (8)
C220.0327 (9)0.0400 (10)0.0345 (9)0.0118 (7)0.0049 (7)0.0039 (8)
C230.0234 (8)0.0386 (9)0.0248 (8)0.0050 (7)0.0004 (6)0.0019 (7)
O240.0312 (6)0.0401 (7)0.0362 (6)0.0060 (5)0.0122 (5)0.0017 (5)
O250.0250 (6)0.0590 (8)0.0432 (7)0.0044 (6)0.0102 (5)0.0079 (6)
C260.0275 (9)0.0489 (11)0.0464 (11)0.0025 (8)0.0014 (8)0.0012 (8)
Geometric parameters (Å, º) top
C1—C81.394 (2)C13—H130.9500
C1—C21.410 (2)C14—C151.376 (2)
C1—N71.414 (2)C14—H140.9500
C2—C111.390 (2)C15—C161.389 (2)
C2—S31.775 (2)C15—H150.9500
S3—C41.848 (2)C16—O251.370 (2)
C4—C121.517 (2)C16—C171.393 (2)
C4—C51.528 (2)C17—H170.9500
C4—H41.0000C18—C191.405 (2)
C5—C61.508 (2)C18—C231.417 (2)
C5—H5A0.9900C19—C201.381 (2)
C5—H5B0.9900C19—H190.9500
C6—N71.297 (2)C20—C211.387 (2)
C6—C181.466 (2)C20—H200.9500
C8—C91.382 (3)C21—C221.377 (3)
C8—H80.9500C21—H210.9500
C9—C101.385 (3)C22—C231.390 (2)
C9—H90.9500C22—H220.9500
C10—C111.385 (3)C23—O241.351 (2)
C10—H100.9500O24—H240.8400
C11—H110.9500O25—C261.422 (2)
C12—C131.386 (2)C26—H26A0.9800
C12—C171.398 (2)C26—H26B0.9800
C13—C141.393 (2)C26—H26C0.9800
C8—C1—C2119.47 (15)C14—C13—H13120.0
C8—C1—N7117.96 (14)C15—C14—C13120.70 (15)
C2—C1—N7122.32 (14)C15—C14—H14119.7
C11—C2—C1118.97 (16)C13—C14—H14119.7
C11—C2—S3118.19 (13)C14—C15—C16119.73 (15)
C1—C2—S3122.19 (13)C14—C15—H15120.1
C2—S3—C4104.57 (7)C16—C15—H15120.1
C12—C4—C5113.73 (12)O25—C16—C17124.64 (15)
C12—C4—S3112.57 (10)O25—C16—C15115.20 (14)
C5—C4—S3109.11 (10)C17—C16—C15120.14 (15)
C12—C4—H4107.0C16—C17—C12119.91 (14)
C5—C4—H4107.0C16—C17—H17120.0
S3—C4—H4107.0C12—C17—H17120.0
C6—C5—C4112.58 (12)C19—C18—C23117.48 (15)
C6—C5—H5A109.1C19—C18—C6121.31 (14)
C4—C5—H5A109.1C23—C18—C6121.09 (14)
C6—C5—H5B109.1C20—C19—C18122.08 (15)
C4—C5—H5B109.1C20—C19—H19119.0
H5A—C5—H5B107.8C18—C19—H19119.0
N7—C6—C18118.12 (14)C19—C20—C21119.12 (16)
N7—C6—C5121.45 (14)C19—C20—H20120.4
C18—C6—C5120.43 (14)C21—C20—H20120.4
C6—N7—C1121.32 (13)C22—C21—C20120.57 (16)
C9—C8—C1120.60 (17)C22—C21—H21119.7
C9—C8—H8119.7C20—C21—H21119.7
C1—C8—H8119.7C21—C22—C23120.80 (16)
C8—C9—C10120.08 (18)C21—C22—H22119.6
C8—C9—H9120.0C23—C22—H22119.6
C10—C9—H9120.0O24—C23—C22117.73 (14)
C9—C10—C11119.98 (17)O24—C23—C18122.29 (15)
C9—C10—H10120.0C22—C23—C18119.92 (15)
C11—C10—H10120.0C23—O24—H24109.5
C2—C11—C10120.89 (17)C16—O25—C26118.63 (13)
C2—C11—H11119.6O25—C26—H26A109.5
C10—C11—H11119.6O25—C26—H26B109.5
C13—C12—C17119.52 (14)H26A—C26—H26B109.5
C13—C12—C4122.16 (14)O25—C26—H26C109.5
C17—C12—C4118.32 (13)H26A—C26—H26C109.5
C12—C13—C14119.99 (15)H26B—C26—H26C109.5
C12—C13—H13120.0
C8—C1—C2—C110.8 (2)C17—C12—C13—C140.9 (2)
N7—C1—C2—C11173.35 (14)C4—C12—C13—C14178.49 (15)
C8—C1—C2—S3171.44 (12)C12—C13—C14—C150.4 (3)
N7—C1—C2—S32.7 (2)C13—C14—C15—C160.4 (3)
C11—C2—S3—C4125.51 (12)C14—C15—C16—O25179.76 (15)
C1—C2—S3—C463.79 (13)C14—C15—C16—C170.8 (3)
C2—S3—C4—C1298.63 (12)O25—C16—C17—C12179.20 (15)
C2—S3—C4—C528.61 (12)C15—C16—C17—C120.3 (2)
C12—C4—C5—C6178.28 (13)C13—C12—C17—C160.5 (2)
S3—C4—C5—C651.70 (15)C4—C12—C17—C16178.90 (14)
C4—C5—C6—N790.11 (17)N7—C6—C18—C19178.34 (14)
C4—C5—C6—C1889.42 (16)C5—C6—C18—C191.2 (2)
C18—C6—N7—C1171.87 (12)N7—C6—C18—C232.4 (2)
C5—C6—N7—C17.7 (2)C5—C6—C18—C23177.14 (13)
C8—C1—N7—C6137.86 (15)C23—C18—C19—C201.4 (2)
C2—C1—N7—C647.9 (2)C6—C18—C19—C20174.72 (14)
C2—C1—C8—C90.1 (2)C18—C19—C20—C210.1 (3)
N7—C1—C8—C9174.31 (14)C19—C20—C21—C221.1 (3)
C1—C8—C9—C100.9 (2)C20—C21—C22—C230.6 (3)
C8—C9—C10—C111.3 (3)C21—C22—C23—O24178.32 (15)
C1—C2—C11—C100.5 (2)C21—C22—C23—C180.9 (2)
S3—C2—C11—C10171.49 (13)C19—C18—C23—O24179.13 (14)
C9—C10—C11—C20.6 (2)C6—C18—C23—O243.0 (2)
C5—C4—C12—C1322.2 (2)C19—C18—C23—C221.8 (2)
S3—C4—C12—C13102.57 (15)C6—C18—C23—C22174.26 (14)
C5—C4—C12—C17157.21 (14)C17—C16—O25—C2617.6 (2)
S3—C4—C12—C1778.05 (16)C15—C16—O25—C26163.49 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O24—H24···N70.841.812.5489 (18)147

Experimental details

(IVa)(IVb)(IVc)
Crystal data
Chemical formulaC21H16ClNOSC22H19NOSC22H19NO2S
Mr365.86345.44361.44
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)173173173
a, b, c (Å)18.036 (9), 4.836 (2), 19.790 (11)4.8678 (11), 17.563 (3), 20.129 (5)11.973 (2), 16.224 (4), 9.250 (3)
β (°) 97.02 (2) 93.078 (8) 94.437 (9)
V3)1713.2 (15)1718.4 (6)1791.4 (8)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.350.200.20
Crystal size (mm)0.15 × 0.08 × 0.060.22 × 0.12 × 0.080.35 × 0.08 × 0.07
Data collection
DiffractometerNonius KappaCCD Area Detector
diffractometer
Nonius KappaCCD Area Detector
diffractometer
Nonius KappaCCD Area Detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Multi-scan
SORTAV: (Blessing, 1997)
Multi-scan
SORTAV: (Blessing, 1997)
Tmin, Tmax0.901, 0.9820.906, 0.9880.908, 0.990
No. of measured, independent and
observed reflections
9054, 2987, 2093 [I > 2σ(I)]8207, 4972, 3195 [I > 2.0σ(I)]7583, 4081, 3007 [I > 2.0σ(I)]
Rint0.0640.0370.031
(sin θ/λ)max1)0.5950.7030.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.113, 1.02 0.046, 0.121, 0.99 0.040, 0.107, 1.02
No. of reflections298749724081
No. of parameters227228237
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.320.23, 0.320.23, 0.36

Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), HKL SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).

Selected geometric parameters (Å, º) for (IVa) top
C1—N71.418 (3)C6—N71.295 (3)
C2—S31.776 (3)C15—Cl251.743 (3)
S3—C41.836 (2)C23—O241.349 (3)
C2—S3—C4103.99 (12)C6—N7—C1121.0 (2)
Hydrogen-bond geometry (Å, º) for (IVa) top
D—H···AD—HH···AD···AD—H···A
O24—H24···N70.841.802.543 (3)146
Selected geometric parameters (Å, º) for (IVb) top
S3—C21.7696 (17)N7—C61.2952 (19)
S3—C41.8368 (15)N7—C11.4128 (19)
O24—C231.3427 (19)
C2—S3—C4103.23 (7)C6—N7—C1120.37 (13)
C23—O24—H24109.5
Hydrogen-bond geometry (Å, º) for (IVb) top
D—H···AD—HH···AD···AD—H···A
O24—H24···N70.841.802.5489 (17)147
Selected geometric parameters (Å, º) for (IVc) top
C1—N71.414 (2)C6—N71.297 (2)
C2—S31.775 (2)C23—O241.351 (2)
S3—C41.848 (2)
C2—S3—C4104.57 (7)C6—N7—C1121.32 (13)
Hydrogen-bond geometry (Å, º) for (IVc) top
D—H···AD—HH···AD···AD—H···A
O24—H24···N70.841.812.5489 (18)147
 

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