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In the title compound, C17H17NOS, the phenyl ring at position 6 of the thia­zine ring is trans to the hydr­oxy group. The thia­zine ring is in a sofa conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007008/bt2020sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007008/bt2020Isup2.hkl
Contains datablock I

CCDC reference: 604979

Key indicators

  • Single-crystal X-ray study
  • T = 190 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.102
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.120 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

4-Hydroxy-4-methyl-2,6-diphenyl-5,6-dihydro-4H-1,3-thiazine top
Crystal data top
C17H17NOSDx = 1.255 Mg m3
Mr = 283.39Melting point: 127 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 10470 reflections
a = 12.1452 (2) Åθ = 3.0–25.0°
b = 10.6688 (2) ŵ = 0.21 mm1
c = 23.1573 (6) ÅT = 190 K
V = 3000.60 (11) Å3Prism, colourless
Z = 80.13 × 0.13 × 0.02 mm
F(000) = 1200
Data collection top
Nonius KappaCCD
diffractometer
1718 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.120
Graphite monochromatorθmax = 25.1°, θmin = 3.1°
Detector resolution: 9 pixels mm-1h = 1414
CCD scansk = 1212
45044 measured reflectionsl = 2727
2663 independent reflections
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) = 0.102H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.045P)2 + 0.1974P]
where P = (Fo2 + 2Fc2)/3
2663 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.81594 (5)0.55786 (5)0.05326 (3)0.0375 (2)
C10.71594 (19)0.57170 (18)0.00148 (9)0.0290 (5)
N10.61358 (15)0.59948 (16)0.00336 (7)0.0310 (5)
C20.56306 (18)0.6240 (2)0.06035 (9)0.0325 (6)
C30.64273 (19)0.6807 (2)0.10381 (10)0.0355 (6)
H10.60210.70110.13960.043*
H20.67240.75990.08790.043*
C40.73817 (19)0.5941 (2)0.11864 (9)0.0331 (6)
H30.70760.51420.13450.040*
C50.76173 (18)0.55117 (18)0.06008 (9)0.0286 (5)
C60.84612 (19)0.4657 (2)0.07018 (10)0.0376 (6)
H40.87520.41770.03920.045*
C70.8878 (2)0.4505 (2)0.12548 (11)0.0440 (7)
H50.94480.39140.13240.053*
C80.8467 (2)0.5211 (2)0.17043 (11)0.0453 (7)
H60.87610.51140.20820.054*
C90.7630 (2)0.6057 (2)0.16081 (10)0.0425 (6)
H70.73450.65380.19190.051*
C100.72078 (19)0.6204 (2)0.10604 (10)0.0348 (6)
H80.66290.67870.09960.042*
O10.52831 (13)0.50708 (14)0.08385 (7)0.0374 (4)
H90.48850.46960.05970.089 (12)*
C110.46573 (18)0.7102 (2)0.05012 (11)0.0421 (7)
H100.49220.79160.03620.063*
H110.42530.72180.08640.063*
H120.41680.67290.02120.063*
C120.81749 (18)0.64817 (19)0.16214 (9)0.0303 (6)
C130.83726 (19)0.5865 (2)0.21393 (10)0.0405 (6)
H130.80080.50950.22170.049*
C140.9094 (2)0.6356 (2)0.25434 (10)0.0473 (7)
H140.92140.59310.28980.057*
C150.9637 (2)0.7461 (2)0.24301 (11)0.0460 (7)
H151.01400.77920.27050.055*
C160.9451 (2)0.8087 (2)0.19189 (11)0.0414 (6)
H160.98210.88550.18430.050*
C170.87288 (19)0.7602 (2)0.15182 (10)0.0352 (6)
H170.86070.80370.11660.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0308 (4)0.0469 (4)0.0348 (4)0.0071 (3)0.0018 (3)0.0044 (3)
C10.0309 (14)0.0249 (12)0.0310 (14)0.0021 (11)0.0007 (10)0.0009 (10)
N10.0302 (12)0.0308 (11)0.0320 (12)0.0003 (8)0.0042 (9)0.0025 (8)
C20.0269 (13)0.0357 (13)0.0349 (14)0.0020 (11)0.0036 (11)0.0036 (11)
C30.0341 (15)0.0386 (14)0.0338 (15)0.0033 (11)0.0056 (11)0.0010 (11)
C40.0341 (14)0.0336 (13)0.0315 (14)0.0023 (11)0.0018 (11)0.0046 (10)
C50.0254 (12)0.0273 (12)0.0331 (14)0.0047 (11)0.0007 (11)0.0017 (11)
C60.0378 (15)0.0381 (14)0.0369 (15)0.0045 (11)0.0005 (11)0.0009 (11)
C70.0376 (16)0.0455 (15)0.0490 (17)0.0053 (12)0.0091 (13)0.0114 (13)
C80.0433 (16)0.0572 (17)0.0355 (16)0.0096 (14)0.0092 (13)0.0063 (13)
C90.0449 (17)0.0489 (16)0.0336 (16)0.0022 (14)0.0004 (13)0.0021 (12)
C100.0301 (14)0.0370 (13)0.0374 (15)0.0011 (11)0.0011 (12)0.0009 (12)
O10.0333 (10)0.0394 (9)0.0394 (10)0.0057 (8)0.0013 (9)0.0082 (8)
C110.0342 (15)0.0457 (14)0.0465 (17)0.0103 (12)0.0032 (13)0.0007 (12)
C120.0297 (14)0.0305 (13)0.0306 (14)0.0034 (11)0.0015 (11)0.0000 (11)
C130.0468 (16)0.0378 (14)0.0367 (16)0.0000 (12)0.0034 (13)0.0068 (12)
C140.0595 (19)0.0507 (17)0.0316 (15)0.0066 (14)0.0055 (14)0.0050 (13)
C150.0478 (17)0.0496 (16)0.0407 (17)0.0051 (14)0.0105 (14)0.0077 (14)
C160.0457 (17)0.0338 (13)0.0449 (17)0.0009 (12)0.0053 (13)0.0059 (12)
C170.0368 (15)0.0349 (14)0.0337 (14)0.0031 (12)0.0015 (12)0.0008 (11)
Geometric parameters (Å, º) top
S1—C11.762 (2)C8—H60.9500
S1—C41.826 (2)C9—C101.377 (3)
C1—N11.283 (3)C9—H70.9500
C1—C51.483 (3)C10—H80.9500
N1—C21.479 (3)O1—H90.8400
C2—O11.425 (3)C11—H100.9800
C2—C111.516 (3)C11—H110.9800
C2—C31.522 (3)C11—H120.9800
C3—C41.522 (3)C12—C131.389 (3)
C3—H10.9900C12—C171.392 (3)
C3—H20.9900C13—C141.385 (3)
C4—C121.509 (3)C13—H130.9500
C4—H31.0000C14—C151.375 (3)
C5—C101.388 (3)C14—H140.9500
C5—C61.392 (3)C15—C161.378 (3)
C6—C71.387 (3)C15—H150.9500
C6—H40.9500C16—C171.378 (3)
C7—C81.379 (3)C16—H160.9500
C7—H50.9500C17—H170.9500
C8—C91.377 (3)
C1—S1—C4102.84 (10)C9—C8—H6119.9
N1—C1—C5118.51 (19)C7—C8—H6119.9
N1—C1—S1128.66 (17)C8—C9—C10119.9 (2)
C5—C1—S1112.80 (16)C8—C9—H7120.0
C1—N1—C2121.39 (18)C10—C9—H7120.0
O1—C2—N1108.00 (17)C9—C10—C5120.8 (2)
O1—C2—C11111.09 (18)C9—C10—H8119.6
N1—C2—C11106.93 (18)C5—C10—H8119.6
O1—C2—C3106.48 (18)C2—O1—H9109.5
N1—C2—C3113.38 (18)C2—C11—H10109.5
C11—C2—C3110.97 (18)C2—C11—H11109.5
C2—C3—C4113.10 (18)H10—C11—H11109.5
C2—C3—H1109.0C2—C11—H12109.5
C4—C3—H1109.0H10—C11—H12109.5
C2—C3—H2109.0H11—C11—H12109.5
C4—C3—H2109.0C13—C12—C17118.1 (2)
H1—C3—H2107.8C13—C12—C4120.4 (2)
C12—C4—C3113.88 (17)C17—C12—C4121.5 (2)
C12—C4—S1107.72 (15)C14—C13—C12120.9 (2)
C3—C4—S1109.60 (15)C14—C13—H13119.6
C12—C4—H3108.5C12—C13—H13119.6
C3—C4—H3108.5C15—C14—C13119.9 (2)
S1—C4—H3108.5C15—C14—H14120.0
C10—C5—C6118.9 (2)C13—C14—H14120.0
C10—C5—C1119.3 (2)C14—C15—C16120.1 (2)
C6—C5—C1121.8 (2)C14—C15—H15120.0
C7—C6—C5120.0 (2)C16—C15—H15120.0
C7—C6—H4120.0C17—C16—C15120.0 (2)
C5—C6—H4120.0C17—C16—H16120.0
C8—C7—C6120.1 (2)C15—C16—H16120.0
C8—C7—H5120.0C16—C17—C12121.0 (2)
C6—C7—H5120.0C16—C17—H17119.5
C9—C8—C7120.2 (2)C12—C17—H17119.5
C4—S1—C1—N10.4 (2)C1—C5—C6—C7179.1 (2)
C4—S1—C1—C5177.61 (14)C5—C6—C7—C80.8 (4)
C5—C1—N1—C2178.61 (17)C6—C7—C8—C90.9 (4)
S1—C1—N1—C20.7 (3)C7—C8—C9—C100.4 (4)
C1—N1—C2—O187.0 (2)C8—C9—C10—C50.2 (3)
C1—N1—C2—C11153.39 (19)C6—C5—C10—C90.4 (3)
C1—N1—C2—C330.8 (3)C1—C5—C10—C9178.6 (2)
O1—C2—C3—C455.2 (2)C3—C4—C12—C13121.3 (2)
N1—C2—C3—C463.4 (2)S1—C4—C12—C13117.0 (2)
C11—C2—C3—C4176.21 (18)C3—C4—C12—C1758.9 (3)
C2—C3—C4—C12179.43 (18)S1—C4—C12—C1762.9 (2)
C2—C3—C4—S159.8 (2)C17—C12—C13—C140.5 (3)
C1—S1—C4—C12152.12 (14)C4—C12—C13—C14179.6 (2)
C1—S1—C4—C327.73 (17)C12—C13—C14—C150.9 (4)
N1—C1—C5—C1033.8 (3)C13—C14—C15—C161.0 (4)
S1—C1—C5—C10144.42 (17)C14—C15—C16—C170.6 (4)
N1—C1—C5—C6147.2 (2)C15—C16—C17—C120.2 (4)
S1—C1—C5—C634.5 (2)C13—C12—C17—C160.2 (3)
C10—C5—C6—C70.1 (3)C4—C12—C17—C16179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H9···N1i0.842.052.888 (2)173
Symmetry code: (i) x+1, y+1, z.
 

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