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In the title compound, the heterocyclic portion of the di­hydro­benzo­thia­zine unit adopts a shallow boat conformation. The propynyl substituent is nearly perpendicular to the plane formed by the rails of the boat. In the crystal, inversion dimers are formed by weak C—H...F hydrogen bonds with the dimers forming oblique stacks along the a-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019002354/lh5893sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019002354/lh5893Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2056989019002354/lh5893Isup3.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019002354/lh5893Isup6.cml
Supplementary material

CCDC reference: 1897371

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.092
  • Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low . 0.953 Why?
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 ..F1 . 2.60 Ang. PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 96 Report
Alert level G PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.002 Degree PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 68 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(2Z)-2-(4-Fluorobenzylidene)-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzothiazin-3-one top
Crystal data top
C18H12FNOSZ = 2
Mr = 309.35F(000) = 320
Triclinic, P1Dx = 1.455 Mg m3
a = 4.0602 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.8983 (5) ÅCell parameters from 4191 reflections
c = 14.2620 (5) Åθ = 3.6–72.3°
α = 117.809 (2)°µ = 2.15 mm1
β = 93.155 (2)°T = 150 K
γ = 94.416 (2)°Plate, light yellow
V = 705.96 (5) Å30.45 × 0.21 × 0.01 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
2595 independent reflections
Radiation source: INCOATEC IµS micro-focus source2256 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.026
Detector resolution: 10.4167 pixels mm-1θmax = 72.2°, θmin = 3.6°
ω scansh = 44
Absorption correction: numerical
(SADABS; Krause et al., 2015)
k = 1715
Tmin = 0.69, Tmax = 0.97l = 1517
5323 measured 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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.092All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.047P)2 + 0.2564P]
where P = (Fo2 + 2Fc2)/3
2595 reflections(Δ/σ)max < 0.001
247 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

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

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 > 2sigma(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
S10.36900 (11)0.48920 (3)0.16432 (3)0.02650 (14)
F10.4439 (4)0.02242 (10)0.11539 (11)0.0500 (4)
O10.6330 (3)0.62345 (10)0.47251 (9)0.0274 (3)
N10.7395 (3)0.69008 (11)0.35897 (11)0.0196 (3)
C10.4638 (4)0.62082 (14)0.17880 (13)0.0216 (3)
C20.3701 (5)0.63770 (16)0.09280 (14)0.0280 (4)
H20.244 (6)0.5760 (19)0.0305 (18)0.040 (6)*
C30.4589 (5)0.73747 (16)0.09560 (15)0.0302 (4)
H30.400 (5)0.7482 (18)0.0363 (18)0.035 (6)*
C40.6386 (5)0.82155 (16)0.18618 (16)0.0309 (4)
H40.717 (5)0.8918 (19)0.1894 (17)0.037 (6)*
C50.7262 (4)0.80684 (15)0.27349 (14)0.0253 (4)
H50.838 (6)0.8665 (19)0.3380 (18)0.034 (6)*
C60.6440 (4)0.70567 (14)0.27073 (13)0.0200 (3)
C70.5847 (4)0.61287 (13)0.38287 (13)0.0201 (3)
C80.3693 (4)0.51633 (13)0.29720 (13)0.0200 (3)
C90.9780 (4)0.77412 (14)0.44531 (14)0.0226 (4)
H9A1.078 (5)0.7384 (17)0.4841 (16)0.027 (5)*
H9B1.157 (5)0.7991 (17)0.4139 (16)0.029 (5)*
C100.8244 (4)0.86876 (14)0.52130 (13)0.0232 (4)
C110.7008 (5)0.94494 (16)0.58223 (16)0.0323 (4)
H110.598 (7)1.005 (2)0.627 (2)0.058 (8)*
C120.2140 (4)0.44701 (14)0.32673 (13)0.0221 (4)
H120.239 (5)0.4694 (17)0.4023 (17)0.027 (5)*
C130.0273 (4)0.33862 (14)0.26424 (13)0.0224 (4)
C140.0509 (5)0.26864 (15)0.15586 (14)0.0273 (4)
H140.190 (5)0.2934 (18)0.1155 (17)0.033 (6)*
C150.1081 (5)0.16234 (16)0.10546 (16)0.0317 (4)
H150.091 (6)0.1127 (19)0.0299 (19)0.041 (6)*
C160.2926 (5)0.12750 (16)0.16410 (17)0.0337 (4)
C170.3307 (5)0.19315 (17)0.26970 (16)0.0334 (4)
H170.461 (6)0.166 (2)0.3075 (19)0.046 (7)*
C180.1680 (4)0.29876 (15)0.31937 (15)0.0258 (4)
H180.184 (5)0.3440 (17)0.3957 (18)0.029 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0385 (3)0.0213 (2)0.0162 (2)0.00484 (17)0.00200 (16)0.00729 (18)
F10.0686 (9)0.0280 (6)0.0495 (8)0.0221 (6)0.0186 (6)0.0217 (6)
O10.0346 (7)0.0275 (7)0.0186 (6)0.0014 (5)0.0013 (5)0.0108 (5)
N10.0214 (7)0.0177 (7)0.0176 (7)0.0015 (5)0.0016 (5)0.0067 (6)
C10.0221 (8)0.0235 (9)0.0208 (8)0.0027 (6)0.0047 (6)0.0114 (7)
C20.0297 (10)0.0330 (10)0.0214 (9)0.0033 (7)0.0040 (7)0.0129 (8)
C30.0378 (11)0.0351 (11)0.0255 (9)0.0094 (8)0.0076 (7)0.0197 (9)
C40.0426 (11)0.0257 (10)0.0311 (10)0.0083 (8)0.0130 (8)0.0173 (9)
C50.0291 (9)0.0214 (9)0.0247 (9)0.0035 (7)0.0070 (7)0.0097 (8)
C60.0190 (8)0.0212 (8)0.0195 (8)0.0044 (6)0.0055 (6)0.0087 (7)
C70.0214 (8)0.0202 (8)0.0182 (8)0.0054 (6)0.0032 (6)0.0080 (7)
C80.0220 (8)0.0178 (8)0.0188 (8)0.0030 (6)0.0025 (6)0.0073 (7)
C90.0198 (8)0.0208 (8)0.0229 (8)0.0001 (6)0.0004 (6)0.0075 (7)
C100.0225 (8)0.0215 (9)0.0227 (8)0.0046 (6)0.0010 (6)0.0095 (7)
C110.0336 (11)0.0231 (10)0.0321 (10)0.0004 (8)0.0083 (8)0.0064 (9)
C120.0259 (9)0.0224 (9)0.0182 (8)0.0044 (6)0.0044 (6)0.0092 (7)
C130.0229 (8)0.0214 (9)0.0248 (9)0.0011 (6)0.0006 (6)0.0131 (7)
C140.0338 (10)0.0230 (9)0.0248 (9)0.0007 (7)0.0035 (7)0.0115 (8)
C150.0413 (11)0.0219 (9)0.0271 (10)0.0005 (8)0.0038 (8)0.0088 (8)
C160.0401 (11)0.0216 (9)0.0393 (11)0.0087 (8)0.0132 (8)0.0178 (8)
C170.0338 (10)0.0346 (11)0.0381 (11)0.0079 (8)0.0064 (8)0.0253 (10)
C180.0273 (9)0.0293 (10)0.0252 (9)0.0007 (7)0.0013 (7)0.0173 (8)
Geometric parameters (Å, º) top
S1—C81.7511 (17)C8—C121.348 (2)
S1—C11.7515 (17)C9—C101.471 (2)
F1—C161.364 (2)C9—H9A0.99 (2)
O1—C71.219 (2)C9—H9B0.99 (2)
N1—C71.387 (2)C10—C111.183 (3)
N1—C61.412 (2)C11—H110.93 (3)
N1—C91.473 (2)C12—C131.461 (2)
C1—C21.391 (2)C12—H120.97 (2)
C1—C61.401 (2)C13—C181.400 (2)
C2—C31.387 (3)C13—C141.404 (2)
C2—H20.98 (2)C14—C151.388 (3)
C3—C41.387 (3)C14—H140.98 (2)
C3—H30.95 (2)C15—C161.373 (3)
C4—C51.385 (3)C15—H150.98 (2)
C4—H40.98 (2)C16—C171.375 (3)
C5—C61.402 (2)C17—C181.386 (3)
C5—H50.96 (2)C17—H170.95 (2)
C7—C81.493 (2)C18—H180.98 (2)
S1···N13.0702 (15)C10···C11vii3.572 (3)
S1···C143.179 (2)C12···C18vii3.343 (3)
S1···C2i3.5158 (19)C13···C18vii3.464 (2)
S1···H142.51 (3)C13···C17vii3.439 (3)
S1···H2i3.06 (2)C14···C17vii3.404 (3)
F1···F1ii3.051 (2)C14···C16vii3.457 (3)
F1···C15ii3.306 (3)C15···C16vii3.495 (3)
F1···H4iii2.59 (3)C4···H11viii2.91 (3)
F1···H15ii2.60 (2)C5···H9B2.63 (2)
O1···C103.167 (3)C5···H11viii2.80 (3)
O1···C18iv3.388 (2)C6···H9Bvi2.85 (2)
O1···C18v3.261 (2)C7···H9Avi2.81 (2)
O1···H122.33 (2)C8···H142.97 (2)
O1···H9Avi2.83 (2)C9···H52.48 (3)
O1···H9A2.26 (2)C10···H52.60 (2)
O1···H12v2.70 (2)C10···H9Bvi2.90 (2)
O1···H18iv2.60 (2)C11···H5ix2.81 (3)
O1···H18v2.71 (2)C11···H9Bvi2.99 (2)
N1···H9Bvi2.85 (2)C11···H17iv2.82 (3)
C5···C103.216 (2)H2···H2x2.57 (4)
C7···C12vii3.448 (3)H5···H9B2.17 (3)
C7···C9vi3.334 (3)H5···H11viii2.52 (4)
C9···C10vii3.504 (2)H9A···H18v2.50 (3)
C9···C11vii3.469 (3)H12···H182.32 (3)
C8—S1—C1101.73 (8)C10—C9—H9A108.6 (12)
C7—N1—C6125.59 (14)N1—C9—H9A106.8 (12)
C7—N1—C9114.59 (13)C10—C9—H9B109.9 (12)
C6—N1—C9118.68 (14)N1—C9—H9B109.3 (12)
C2—C1—C6120.19 (16)H9A—C9—H9B108.7 (17)
C2—C1—S1117.64 (14)C11—C10—C9179.8 (2)
C6—C1—S1122.07 (13)C10—C11—H11177.1 (17)
C3—C2—C1120.78 (17)C8—C12—C13131.55 (16)
C3—C2—H2122.1 (14)C8—C12—H12115.9 (12)
C1—C2—H2117.1 (14)C13—C12—H12112.4 (12)
C4—C3—C2119.25 (17)C18—C13—C14117.96 (16)
C4—C3—H3120.1 (14)C18—C13—C12116.92 (16)
C2—C3—H3120.7 (14)C14—C13—C12124.90 (16)
C5—C4—C3120.61 (17)C15—C14—C13121.06 (17)
C5—C4—H4117.9 (13)C15—C14—H14118.9 (13)
C3—C4—H4121.4 (13)C13—C14—H14119.9 (13)
C4—C5—C6120.64 (17)C16—C15—C14118.26 (18)
C4—C5—H5120.7 (14)C16—C15—H15120.2 (14)
C6—C5—H5118.6 (14)C14—C15—H15121.5 (14)
C1—C6—C5118.49 (16)F1—C16—C15118.42 (19)
C1—C6—N1120.91 (15)F1—C16—C17118.38 (18)
C5—C6—N1120.60 (15)C15—C16—C17123.20 (18)
O1—C7—N1119.59 (15)C16—C17—C18117.97 (18)
O1—C7—C8121.15 (15)C16—C17—H17120.7 (15)
N1—C7—C8119.23 (14)C18—C17—H17121.4 (15)
C12—C8—C7116.29 (15)C17—C18—C13121.53 (18)
C12—C8—S1123.30 (13)C17—C18—H18117.9 (12)
C7—C8—S1119.93 (12)C13—C18—H18120.5 (12)
C10—C9—N1113.47 (14)
C8—S1—C1—C2157.17 (14)N1—C7—C8—C12177.04 (15)
C8—S1—C1—C626.38 (15)O1—C7—C8—S1167.49 (13)
C6—C1—C2—C31.4 (3)N1—C7—C8—S110.7 (2)
S1—C1—C2—C3175.12 (14)C1—S1—C8—C12159.13 (15)
C1—C2—C3—C41.1 (3)C1—S1—C8—C729.17 (15)
C2—C3—C4—C50.6 (3)C7—N1—C9—C1087.21 (18)
C3—C4—C5—C62.0 (3)C6—N1—C9—C1081.32 (18)
C2—C1—C6—C50.0 (2)C7—C8—C12—C13169.96 (16)
S1—C1—C6—C5176.34 (13)S1—C8—C12—C132.0 (3)
C2—C1—C6—N1179.64 (15)C8—C12—C13—C18165.58 (18)
S1—C1—C6—N14.0 (2)C8—C12—C13—C1419.9 (3)
C4—C5—C6—C11.7 (3)C18—C13—C14—C151.5 (3)
C4—C5—C6—N1178.67 (16)C12—C13—C14—C15172.96 (17)
C7—N1—C6—C123.7 (2)C13—C14—C15—C160.7 (3)
C9—N1—C6—C1169.12 (14)C14—C15—C16—F1178.73 (17)
C7—N1—C6—C5155.92 (16)C14—C15—C16—C170.8 (3)
C9—N1—C6—C511.2 (2)F1—C16—C17—C18178.11 (17)
C6—N1—C7—O1162.11 (15)C15—C16—C17—C181.5 (3)
C9—N1—C7—O15.5 (2)C16—C17—C18—C130.6 (3)
C6—N1—C7—C819.7 (2)C14—C13—C18—C170.8 (3)
C9—N1—C7—C8172.72 (14)C12—C13—C18—C17174.05 (16)
O1—C7—C8—C124.8 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z; (iii) x1, y1, z; (iv) x, y+1, z+1; (v) x+1, y+1, z+1; (vi) x1, y, z; (vii) x+1, y, z; (viii) x+1, y+2, z+1; (ix) x+2, y+2, z+1; (x) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···F1ii0.98 (2)2.60 (2)3.306 (2)128.5 (17)
Symmetry code: (ii) x1, y, z.
 

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